


NSFW SPN One-shots

by infinite_nat



Category: Supernatural
Genre: F/M
Language: English
Status: In-Progress
Published: 2017-06-12
Updated: 2017-07-18
Packaged: 2018-11-13 11:27:36
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 13
Words: 25,608
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11184153
Author URL: https://archiveofourown.org/users/infinite_nat/pseuds/infinite_nat
Summary: Everything inside is one-shots, NSFW, filthy smut, and reader-insert. The first eleven chapters were transferred from my tumblr blog (just-a-supernatural-smut-blog) *** My work is not to be reposted on any other site without my written permission***





	1. See Me Come - Dean Winchester

**Summary for the Chapter:**

> Requested from Tumblr: Dean walks in on the reader using a toy.

The moment you shut your door, you immediately walked over to your dresser where you kept a little box hidden. Inside the box were some of your favorite toys. Grabbing one of the rather quite large dildos and a pair of headphones, you laid on the bed and opened up a browser on your phone. Typing in one of your favorite porn sites, you scrolled through some of the videos until one caught your eye.

It was only after plugging in the headphones that you opened the video. In the video the couple started out slow. So you began to palm your breasts through your thin tank top, feeling your nipples slowly harden underneath your palm. You watched the couple in the video, their actions becoming less gentle and more frantic, desperate even. One of your hands slipped underneath your tank top, skirting your ribs as you began to play with your nipples.

Biting down on your lip, you kept your eyes on the couple in the video as you slowly began to pull on your nipples. Moaning softly, you continued until your panties were soaking wet. Teasingly you let your hands wander your torso, ran them along the waistband of your shorts, before you decided to tug your shorts down. Your hand came in contact with your panties. So damn soaked.

You whimpered, biting down on your lip. The couple had started the foreplay, the male fingering the female as she gripped onto his hair and moaned. An image flickered in your mind. You in the same position as the female, only you were being finger-fucked by Dean Winchester. A louder moan left your mouth as you let your fingers slide into your panties, spreading your soaked folds.

It was now the thought of Dean getting you off that made you slip your fingers into your heat and groan out loud. The thought of his fingers instead of yours massaging your velvet walls turned you on more than the video. Imagining the male groans coming from the video as the female began sucking him off were actually Dean's groans. His voice in your ear, telling you how pretty you looked spread out on the bed, panties hanging by your ankle.

More moans fell from your lips and eventually, your fingers weren't enough anymore. You blindly reached out for the dildo and pressed it against your folds, sliding it along your slit until it was soaked in your arousal. Only then  did you let it slide into your wet heat, moaning softly. Slowly you slid it in and out of you, trying to relax to the feeling of the dildo stretching you.

At this point you'd dropped your phone. The headphones were still attached, male and female moans filling your ears. It spurred you on as you thrust the dildo inside you. One hand flew to the headboard once you started fucking yourself harder. Biting down on your lip, you muffled the cries that were leaving your mouth. Your legs trembled as your orgasm slowly approached. That's when his name slipped from your lips on instinct. Though you were getting off on porn, you ached for his touch. His mouth, his fingers... His cock...

As you began to hurry your pace, you felt a gaze on you. Eyes flying open, your hand stilled as your gaze landed on the figure leaning against the door. His arms were crossed, a smirk on his lips as he watched you with lust-filled eyes. No words left your lips. You were frozen to the spot, unable to move.

When you finally found your voice, you croaked out, “Dean.”

He shook his head, his smirk growing. “Nuh-uh, sweetheart. Keep going. I'm enjoying the show.”

You wanted to ask how long he'd been there, but by the look on his face told you he'd been watching for quite some time. After yanking the headphones from your ears, you continued pumping the dildo in and out of you. But as you did, your gaze never left his.

Dean licked his lips as he watched you. “Keep going. Until you come.”

You whimpered as another flood of arousal hit you. Getting yourself off in front of the man while he never touched you had to be one of the hottest things you’ve done so far. So with a flick of your wrist, you were hitting the perfect spot over and over. One hand flew to the headboard to ground yourself as your back arched.

With one more thrust, you came loud and hard. You trembled and shook as you pushed yourself through your orgasm, riding out the waves of pleasure as you panted. Moments later, Dean was pulling the dildo out of you and setting it aside.

He kissed your lips gently, brushing hair away from your face. “You were such a good girl for me, did just as I asked. D’you want me to fuck you now? Reward you?”

You shook your head. Still too sensitive from your orgasm and it’s been so long since you last touched Dean.

“Not yet,” you whispered, hands traveling to his southern regions.

Almost immediately, you saw his eyes light up. After a minute of catching your breath, you switched places. Dean was now underneath you as you crawled down his body. You fiddled with the button of his jeans before tugging them down his hips. Already a prominent bulge was displayed.

Grinning you leaned down and started palming him through his briefs. His head fell back as a soft, almost inaudible. When you finally dug your fingers into the waistband and pulled them down, you immediately bit down on your lip. Fuck, Dean was absolutely perfect. You couldn't wait to get your lips around him.

Taking his cock in your hand, you licked a bold stripe from base to tip before engulfing him in your mouth. Instantly he had his fingers in your hair, gripping it tight as you began to move up and down on his cock. You groaned around his cock when he tugged on your hair rather hard. Profanities slipped from his mouth as his hips bucked forwards, beginning to fuck your mouth relentlessly.

So you relaxed your jaw and rested your hands on either side of his hips, occasionally moaning around his cock. It wasn't long before you felt him tense up in your mouth. So you hollowed your cheeks and sucked, feeling hot spurts of come fill your mouth only seconds later. His grip on your hair tightened as he groaned your name quietly.

After swallowing everything, the first thing you did was put on a t-shirt you knew would fall down to your thighs and sneak out to kitchen after kissing Dean on the cheek. Sam, fortunately, was nowhere to be seen. You grabbed a couple water bottles and headed back to the room where you tossed one at Dean.

That was definitely not the first time either of you would be coming tonight.

Without even sitting up, Dean downed three-quarters of his by the time you finished half of yours. After capping his bottle, he tossed to the floor and grabbed you by your hips. He pulled you back to the bed, crashing right on top of him. You groaned and only managed to get half of your body off him before he stopped you. Legs sprawled over his and one arm still draped across his chest, Dean had tilted your chin up and kissed you deeply.

Everything shifted from frantic and heated to soft and gentle. You cupped his jaw and kissed back, tongue swiping across his bottom lip. All you wanted now was to feel him. There was nothing frantic about it. You wanted to feel his arms envelope you as you kissed him, to feel his length harden against your thigh... Just skin against skin.

So Dean shifted himself that his cock was pressed against your slick folds. Hooking your leg higher on his hip, he slowly entered you while you kept your mouths locked. You moaned into his mouth as he slowly rocked his hips against yours, clutching onto him tightly. He pulled away, panting as he continued to slowly make love to you.

As he tangled one hand in your hair, he brought your faces close enough that your foreheads touched and his breath tickled your mouth.

“Fuck,” he murmured quietly, “Fuck, Y/N, I’ve missed you.”

You cupped the back of his neck, a soft moan leaving your mouth as he hit your spot just perfectly. “Dean... Missed you too...”

Soft murmurs in between pants and moans was all that could be heard besides the obscene, slick noises. And this time, you both slowly climbed towards your orgasm together while clutching each other tightly. A small whine left your lips, warning him only moments before you came. Softly crying you trembled under his touch and brought him over the edge with you. He groaned your name against your lips, holding you tightly.

A few minutes after you both came down from your high the only movement either of you made was a shifting of Dean’s hips to slide out his softened member. You buried your face into Dean’s neck before murmuring an “I love you.”


	2. Worth It All - Castiel

**Summary for the Chapter:**

> Castiel has his own way of getting information out of the demon (requested from Tumblr).

**Notes for the Chapter:**

> Chapter warnings: Dom!Cas, bound, partial suspension, gagging, spanking, a touch of biting, cursing, dirty talk, orgasm denial / edging,

_Shit._

The moment they walked through the diner’s doors, you knew you had to somehow up and leave without drawing attention to yourself. You’d managed to hide away from hunters this long, and now they were walking into your meatsuit’s workplace. The Winchesters - the worst of the hunters. You knew them just as well as any other demon.

They were the worst and they were here for you, no doubt about that. You had answers for their questions and you were not willing to answer a couple of ridiculous ass hunters.

You turned to Sara, a coworker. “Hey, do you mind getting that table for me? I have to use the restroom real quick.”

Sara was a nice girl and knew she would say yes. So when she nodded her head, you disappeared to where you could watch the scene unfold and the Winchesters wouldn’t find you.

She walked over to the pair and greeted them with a smile. You watched Sara’s body language as the two greeted her, watching for anything that would give you a hint to run away. They were both grinning, so immediately you didn’t see anything tip you off. Until you saw Sara’s body tense up.

Shit. Of course they knew you were here. Time to go.

And then you were booking it, tossing the apron wrapped around you aside. There was a few looks, especially by the people who were working there, but you didn’t even care. You needed out. There was no way you were being taken by them. You’d rather be killed.

Yanking open the back door, you were heading straight for the little hideout when a hand was placed over your mouth. Wait, no. Not a hand. A gag. Just as you were about to throw a few punches, your hands were easily bound. A muffled growl escaped you.

But you were tossed around and suddenly, you were facing someone you hoped you’d never face.

Castiel.

You heard about this particular angel. Of course there were whispers about him, an angel with the Winchesters. Protection. You were not a high-ranking demon. You were a low-level demon who was left to wreak havoc on the world, cause as much damage as you could. That was your place in this world. Hell, it wasn’t even enough to be a crossroads demon. You were a pathetic demon, and you were fuckin’  _frightened_ when you ran into the Winchesters, because it meant meeting  _him_. Castiel.

His human form was somewhat attractive, when it came to humans at least. Dark hair and vivid blue eyes - eyes more brilliant than other humans. He was dressed in a suit and a trenchcoat. Hmm... Would he wear anything else?

“Got her, Cas? Oooh, good,” you heard the voice of Dean Winchester behind you.

You whipped around to glare at him. God, if you weren’t bound and gagged you would have made a witty or sarcastic remark. Something, anything, to make him eat his words. Stupid hunter.

You knew your eyes flashed black, you could tell in Dean’s face. It went sort of rigid and cold, but Sam Winchester clapped him on the back. You were dragged back to the black car, the Impala, and forced into the back seat beside Castiel. Lovely.

What do you get when you put a demon in a car beside an angel? Silence. Because the fucking demon is bound and gagged. When you were free, you were going to get them back. You were a demon who’d been easily bound and gagged. This was absolutely pathetic, you could do better than this.

But you were stuck inside a car with an angel right beside you.

* * *

Gagged and bound, they traveled all the way to an abandoned house where they dragged you to the basement. Your eyes immediately flickered to the devil’s trap painted in red. In the middle was a chair. This much, you’d expected.

Maybe they’d cut your skin with that special knife of theirs. Or an angel blade. They might use holy water, pour it over your skin or drown you with it. Burn your throat and mouth. Shit, they might even threaten to do an exorcism.

Dean moved to shove you towards the chair, but a hand shot out to stop him. Castiel’s hand.

“Dean, wait,” he said. Every pair of eyes were on him. “This one... she’s not going to crack. Lemme try. Alone.”

He quirked an eyebrow. “Alone?”

Castiel nodded his head. “Trust me with this one.”

Your eyes stayed on the Winchesters’ backs as they walked out of the basement. Nervousness when it came to the Winchesters? Psh, no. Never in a million dreams would the Winchesters make you shake and tremble. The Angel, however.... He was a different story. You expected him to be all good and shit, to be the Lord’s warriors or some bullshit -  _however_ it went. But you knew the whispers about Castiel. He was something different. A force to be reckoned with.

And now, as you heard the tires against gravel outside, you were completely and a hundred percent alone with him. No matter how loud you screamed, no one would hear you.

You swallowed the lump in your throat as you stood in the devil’s trap. Castiel said nothing as he moved around and moved the chair out of reach. This confused you. Normally, they use the chair to torment--

All thoughts were cut off as Castiel grabbed the rope on a table with torture instruments. Eyes wide, he came towards you. He stopped when he was just a foot away, He didn’t undo the previous bounds until you were bound with the rope. Then, he cut them off with a switchblade. Castiel took the end of the rope and tied it tightly to the bars on the ceiling, so you were forced to stand.

The Angel reached up and slowly untied the gag around your mouth. Immediately you sucked your bottom lip in between your teeth. You couldn’t help but notice Castiel’s gaze flicker to your mouth.

“This is how we’re going to do things,” Castiel said as he walked around the Devil’s trap, never quite stepping in. He slid the tan trench coat off his shoulders, revealing a black suit and a blue tie. “You’re going to answer my questions. If you do, you get rewarded. If not, you’ll get punished.”

Without thinking, you replied with a snort, “What are you gonna do, spank me?”

The moment they left your lips, you regretted them. Sometimes you did have a problem with speaking without thinking twice. They didn’t get you in trouble a lot of the time, but in this case, you were worried. You were in a room alone with Castiel, and you weren’t sure how he was going to react.

You watched as he circled the devil’s trap. He didn’t say anything. You heard his footsteps when he disappeared from your vision. But one thing you didn’t see coming was the sharp slap to your bottom. Gasping, you arched your back as Castiel came back into sight.

With almost a mischievous glint in his eyes, he murmured, “Yes. If it’s required, I will spank you till you’re red and sore.”

Immediately, you clenched your thighs together and cursed the fact that you were still wearing that damn waitress skirt. A green shirt and a black skirt was the uniform for the diner. You could have cared less, but now? With your panties getting soaked, you wished you would have worn jeans or a pair of fucking slacks - anything but this damn skirt.

Castiel said nothing as a corner of his mouth lifted into a slight smirk. After a minute of circling the devil’s trap, he stopped as he stood in front of you.

“Perhaps I should give you a preview of what a reward looks like?” he asked, cocking his head to the left.

The Angel didn’t give you enough time to answer. He stepped forward and pressed his entire body against you as his hands easily found your hips. His mouth slanted over yours. The kiss was hot and demanding, nothing you’d expect from an Angel of the Lord. You thought he’d be soft and gentle - nothing like you were experiencing.

And you hated the way it was affecting you. You wanted to push away and not respond, but you couldn’t. It felt too good. His lips were perfect. Just as you began to kiss back, Castiel completely removed himself and stepped out of the devil’s circle.

When you could see his face again, he wore a full grin. Cursing silently, you promised not to divulge any information so easily. You couldn’t let a fucking angel get to you this easily. You were a damn demon!

“You know which demon we’re looking for,” Castiel stated as stood stock still in front of you. His eyes roamed over your face as he continued speaking. “I want to know where he’s hiding out.”

Your eyes flashed black in defiance as you pursed your lips tightly together.

Castiel shook his head. “Come on, Y/N. We need to know where he is. This demon has valuable information on someone we want found. I’m sure you can tell me, right?”

You raised your chin, refusing to answer.

The Angel moved behind you, grabbing a handful of your hair and tugging it back. You felt his breath on your now-exposed neck. For a moment, that’s all you felt with his fingers tightening their grip on your hair. But then, you felt his lips glide over the crook of your neck gently before he bit the skin there.

With a shuddering gasp, you attempted to pull away from Castiel but he still had a grip on your hair.

“Uh, uh, uh,” he tsked you, pulling you back against his chest. “Are you ready to behave? You know if you’re good enough, I can make you orgasm. And if you’re really good, I can fuck you senseless. All you have to do is say the magic words.”

You were tongue-tied. On one hand, you understand that he was an angel. That you were a demon and  _this_ was very, very wrong. If word got out something like this happened and you  _allowed_ it, it would be very, very bad. ‘Pissed’ would be an understatement.

But Castiel... fuck, he was making you feel things you didn’t know you could feel. Your panties were practically drenched by now. Completely aroused, you wanted to say yes. To tell him everything he wanted to know. Getting fucked senseless by an Angel... it turned you on more than you wanted to admit.

So you admitted, “He’s on the west coast.”

“Good girl,” Castiel murmured in your ear. “I think you deserve to be rewarded.”

He let go of his grip on your hair, pushing the locks aside. Tugging your work shirt up, he revealed the smooth skin of your torso. Castiel pressed his hand flat against your stomach as he leaned down and pressed small kisses to the crook of your neck and shoulder. Your head fell back, resting against the angel’s shoulder, as you sighed. Slowly, Castiel’s hand rose as it slipped underneath the tank top you wore and then the bra. His warm hands fondled your breasts, massaging them slowly and gently. You couldn’t help yourself - a soft moan was ripped from you.

You felt the grin grow on his face as he kissed your skin. But then, his fingers rolled your hard nipples between his forefinger and thumb, pinching them gently. A louder moan escaped you as you arched your back, pressing your breasts into his hands even more.

But then his other hand pressed against your stomach and began going lower. Your eyes widened in shock as his fingers reached the lining of your panties. Just when you thought his hand would move upwards, he slipped his hand beneath the waistband and found your aching core.

Breathing heavily, you shut your eyes and let the pleasure wash over you as he circled your clit. He pressed harder and quickened his movements. You felt the familiar coil and warmth, immediately wanting to clutch onto to the angel.

Panting, you cried out, “Fuck! I think I’m gonna-”

Just as you were going to come, Castiel pulled away completely.

“No,” he told you, gripping your hair again. “You don’t get to come. Not without my permission.”

His words only pissed you off. He did warn you if you were good enough, he’d let you orgasm. It meant that there was a possibility you wouldn’t come tonight. This angel would tease you over and over again until he got the information and wouldn’t let you orgasm in the end.

“You know which words I need to hear if you want to come like a good girl,” he whispered in your ear.

In defiance, you kept your mouth shut.

“C’mon, Y/N, I know you know where he is,” Castiel whispered, nipping at her earlobe.

You dug your teeth into your lips, refusing to make a sound.

Castiel sighed and let go of your hair. Your skirt was hitched up, bunched up at your waist as he yanked down your panties. Then it came. A moan was ripped out of you when a hand came down on your ass. Immediately, your teeth bit down harder. This, of course, only made Castiel spank you harder.

Three spanks in, and you were damn near trembling. You wanted to moan, to make a sound, but you didn’t want to give the angel the satisfaction. Another swat to your ass had you arching your back. Your cheeks were probably a bright red by now in the shape of Castiel’s hand.

And you fucking loved it. The thing was though, you knew Castiel knew how much you were enjoying this. He felt how you soaked through your panties when he slid them down your legs.

“Say something,” he murmured in your ear, squeezing your hips. “I know how much you’re enjoying this. How much you love being at my mercy, how much you want to orgasm with my fingers in your cunt. Or better yet, with my cock inside you.”

That’s what finally broke you down. That dirty mouth of his. You had no idea an angel could speak like that. Obviously you were mistaken.

“Fuck,” you whimpered. “He’s in Sacramento, California. In an old abandoned building. Please, please, please.”

“Please what?”

“Fuck me,” you threw your head back, moaning. “Please, fuck me. I want you so bad, Castiel.”

“Was that so hard?” he asked as he came around to face you. He pushed a few locks of hair that fell into your eyes. “You could have saved so much time, Y/N.”

Castiel’s hand gripped the back of your thigh tightly as he wrapped it around his waist. Then, he pressed himself against your chest. You felt his hard cock pressing against the seams of his pants. It made you want him even more, enough that you damn near rocked your hips against his just to get some friction. The only thing stopping you was punishment. He’d punish you if you even attempted to do something like that, you were sure.

“I’m sorry,” you breathed. “I’ll be good. I promise.”

Instead of responding, Castiel pressed his other hand to the back of your neck before leaning in and kissing you. His lips moved against yours slowly and carefully, as if he was planning his every move. You kissed back, wanting nothing more than to wrap your arms around him and pull him even closer, but your arms were bound above your head.

As he kissed you, Castiel grabbed your other leg and locked it around his waist. His clothed length was pressing against your thigh, teasingly. You whimpered against his lips. You had enough foreplay. All you wanted was his fucking cock.

Pulling away, the angel looked you straight in the eyes. You stared back, with nothing but want and need. He may have been an angel, but he could have also been human and you still would have let him fuck you, if he still made you feel like this. All you wanted was him and his cock pounding into you.

Finally, Castiel let your legs drop back down to the floor as he fumbled with his belt. Moments later, the sound of a zipper echoed around the basement, followed by the thud of clothes hitting the floor. You watched as he stepped inside the Devil’s Trap and scuffed part of the spray paint.

You felt it.You could free yourself and get the hell out of there. Or you could stay and have the best sex of your existence.

Castiel leaned forward and untied the rope from the ceiling, but kept your wrists bound. For a moment, he stepped back and gave you the opportunity to leave. It was there, an open window.

But you refused to take it.

You kinked an eyebrow at him.

Immediately, Castiel pressed you against the closest wall and nudged his knee between your legs. You sucked your bottom lip between your teeth to hold in the moans. But he wasn’t having your silence. His lips glided across the point between your shoulder and neck, kissing and sucking lightly before he nipped at the skin.

You moaned and pushed your hips against his crotch, grinding against him. You whispered, “Please.”

“Well since you’ve been so good for me,” he murmured against your ear.

The moan that left your mouth was loud as Castiel pressed his hard cock against your folds. He slid his length up and down your folds until he was soaked in your juices. Then, Castiel slowly slid in until he was fully seated, grunting low in your ear. Your little moans and heavy panting spurred Castiel on as he started thrusting, starting a slow pace.

Your hands tightened into fists when his pace began to pick up until it was a fast, unrelenting pace. His hips met the soft skin of your ass with every thrust, an audible ‘ _slap-slap-slap_ ’ sound filling the room along with your moans. You could feel the orgasm building quickly as his cock slid in and out of you with ease.

Your moans turned into whimpers when Castiel gripped and massaged your breasts, pulling you against his chest. The coil was tightening, your orgasm building quickly until you were just about to be pushed over the edge.

“Please,” you whispered, remembering his words from earlier. “Please, can I come?”

Castiel groaned out, “Come. Come for me.”

His permission was all you needed. You were pushed over the edge, coming while the angel’s name fell off your lips repeatedly. As you panted softly, Castiel still thrust into you sloppily as he chased his orgasm. You felt him as he finally came inside you, his quiet moans muffled as he buried his face into the crook of your neck.

For a moment, neither of you moved as you tried to catch your breathing. But then Castiel slid out of you and straightened your clothes gently. When you were decent again, he turned you around so you were face to face as he untied the rope around your wrists. They were a little pink but nothing too terrible.

Castiel said nothing but nodded his head towards the stairs. He was letting you go free. You knew you should take it before the Winchesters got back, it was stupid not too. But you couldn’t help but stare at him for a moment.

This angel was quite impressive. Intimidating and definitely nothing you expected. No angel would screw a demon like he just did. In fact, no angel would  _touch_ a demon like he touched you. But he did. He fucked you and made you feel things no one else would probably make you feel.

There was something about Castiel that made you want to lay him down on a bed and mess around in the sheets all night, angel or not.

So before you walked out, you leaned forward and pressed your lips to his cheek softly.

You didn’t know if you’d ever see him again. Maybe other demons would find out what happened between you. Maybe the angels. There was a possibility you’d get killed after this. But there was a small secret you were willing to hide away forever:

You didn’t care. It was worth it.


	3. Mine - Dean Winchester

**Summary for the Chapter:**

> Dean is jealous and all he wants is for you to be his.

Dean walked past the front of Baby as he pocketed his keys while reaching for the Motel key card. A night at the bar with Sam after a successful hunt. You joined for the first hour and a half, but left claiming you had a headache and would be in the second motel room you rented if something happened.

He thought about checking up on you when he neared your door. But just as he decided to let you be, a loud moan escaped from your motel room. Eyebrows raised into his hairline, he completely froze. It was unmistakably your voice, your moans. Another high-pitched moan came from the other side of the door.

“Dean,” Sam called his brother’s name. His gaze moved from the door to Sam. “C’mon, leave Y/N alone.”

But just as he was about to move away from your door, your voice sounded again. Only you were moaning another man’s name, a name that wasn’t Dean’s. Anger shot through him, clenching his fist tight as he fought the urge to break through your door.

He said nothing to Sam as he unlocked the door and stormed in.

_Great_ , he thought as he plopped down on the bed, _my night’s ending perfectly_.

* * *

 

Matt was panting as you climbed out of the bed and hurried to the shower. You wanted nothing more than to wash away the sweat. Plus the man was so focused on chasing his own orgasm, he failed to bring you to yours. So you did the next best thing -- you faked it.

Honestly you thought Matt was good. He was sweet and kind, had a lot to talk about with you and was very attractive. But you were wrong. Apparently he couldn’t get you off like you thought he could.

After cranking the shower knobs to a hot, nearly scalding temperature you jumped in the shower. It took you nearly forty minutes to finish your shower and get yourself off. By then, you were sure Matt had left. He had enough time to gather himself, get dressed and leave. But when you opened the bathroom door he was passed out with only his boxers on.

Groaning, you quickly grabbed your phone and messaged Sam.

_So I might have an issue here. Brought someone over, but he passed out while I showered. Can I bunk with you or Dean? Please?_

While you waited for an answer, you dressed in a pair of shorts and a large Black Sabbath t-shirt. When you finished brushing your hair and pulling it up, your phone dinged.

_Dean passed out already but you can bunk with me. - Sam_

With a relieved sigh, you grabbed your phone and motel key card before heading over to the room next door. Knocking softly, the door was quickly pulled open by Sam. He greeted you with a smile before letting you in.

In the bed by the window was Dean sprawled over the bed, still dressed in jeans and his t-shirt, with his face buried in the pillow. You fought a sigh before crawling into Sam’s bed, pulling the covers over you. Sam laid next to you, keeping a decent amount of space between the two of you.

It was late, you were tired and Sam happened to be radiating warmth (seriously, the man was practically a heater). You fell asleep quickly.

When you woke up, there was a sound of a door shutting. Groaning, you lifted your head off the pillow, glancing around the motel room. Dean was sitting at the table, flipping through an older book.

“Morning, princess,” Dean greeted you gruffly.

Rubbing the sleep out of your eyes, you grunted back a reply. Squinting, you realized Sam wasn’t there. Him leaving was what probably woke you up. When you were fully awake, you snatched a breakfast sandwich off the table and began eating.

“Sounded like you had a good night,” Dean grumbled, flipping another page of the book in his hands. “What’re you doing sleeping in here when you got a motel room to yourself?”

You narrowed your eyes at him, wondering who pissed in his cheerios. He was angry and completely rude to you, and for what? His attitude was unnecessary.

“For your information,” you snapped as you got up from the bed, gathering your belongings. You weren’t gonna stick around with his nasty attitude. “I spent last night in Sam’s bed because the guy in my room couldn’t be bothered to get me to come, much less leave.”

You stood and was by the door in three strides, but Dean’s fingers folded around your wrist and pulled you back.

“I’m sorry,” he breathed, pulling you into his chest. Dean buried his face into the crook of your neck, his hands gripping your hips. “I’m sorry for being a jackass. But... I hate the thought of other men getting to touch and please you. I don’t deserve you, but god, I want you to be mine. Mine to touch, to please, to kiss... _All mine_.”

A noise left your mouth, somewhere between a moan and a whimper. Automatically your hand rose to run your hand through his hair, soft in between your fingers. A soft sigh from Dean tickled your neck.

“Show me,” you whispered quietly. “Show me how you’d please me if I was yours.”

Immediately he pulled back and looked you in the eyes, searching for any signs of your words being lies. When he found none, he cupped your cheek and pulled you in for a kiss. At first it was gentle, testing the waters and how it felt. But as minutes passed, the kisses became fierce and hungry. Dean gripped your hips tighter as you clung onto his t-shirt, wanting him closer.

It was only after you were tugging him towards his bed when he pulled away, panting. He asked, “Are you sure you want this?”

You nodded. “Yes. Please. I want _you_.”

With that, he heaved your shirt over your head and let it land somewhere in the motel. Dean pushed you towards the bed and let you drop on it, bouncing once or twice, before he crawled on top of your body. He trailed soft, lingering kisses along your body until he peppered kisses across your collarbone, then your jaw until he met your lips with his.

You moaned out in surprise when Dean rocked his hips against yours. Straining against his jeans was a very prominent bulge. He ground his hips against yours, receiving another moan from you.

“God, your pretty little moans,” Dean murmured against your ear, “they sound so much better now than they did last night.”

“Well I’m not faking them, now, am I?”

“You’ll never have to fake _anything_ when you’re with me.”

All conversation was cut off by another moan. Dean ground his hips against yours slowly until your panties were drenched. All you wanted was his skin against yours, sweaty or not, and his hardened cock inside you. So you tugged on his shirt, running your fingers underneath and across his chest.

Moments later, his shirt was on the floor of the motel room followed by his jeans and boxers. Dean crawled down your body until he was able to hook his fingers in the waistband of your shorts, pulling them down along with your panties. The tips of his fingers lightly trailed along your calves, past your knees, and along your thighs.

Just as you wondered what he was going to do, you felt his fingertips at your folds. Teasingly he ran his fingers along your mound, never quite going anywhere you wanted him. You shifted your hips, his fingers just barely grazing your clit. A frustrated groan left you as you tangled your fingers in your hair.

“Dean, please!” you cried out.

You heard him chuckle. Two of his fingers slowly eased into your wet cunt, curling slightly. In response to his quickening pace, you arched your back and cried out his name loudly. In that moment, you knew you were being loud but you didn’t really care. All that mattered was Dean.

That familiar coil in your stomach made your muscles tighten, your moans turned to heavy breathing and soft whimpers of Dean’s name rolling off your tongue. One hand gripping the sheets, the other in your hair, you wanted to tell him you were close but it seemed he already knew.

His fingers curling against your g-spot, you felt his mouth on your clit suddenly. A surprised cry left your mouth as you felt yourself falling over the edge, coming all over Dean’s fingers.

Catching your breath, you felt Dean move around on the bed. But you kept your eyes closed because that was one hell of an orgasm. It was nothing like last night’s, just a simple quick flick of your fingers over your clit just to get some type of release.

Then you felt him at your side, dropping an arm over your waist and pulling you against him. His hard length was pressed against your hip, practically begging for attention. But he cupped your cheek and slowly kissed you. You responded eagerly, placing a hand at the nape of his neck.

Dean threw your leg over his hip and pulled his mouth away from yours as he slowly entered you. Breaths mingling, a small groan left your mouth when he was fully seated inside you.

The pace was slow, you and Dean clinging to each other. The kisses were long and intense, moans and whimpers mixed within. It was quite unlike anything you’ve ever experienced. It was more passionate with Dean than you’d ever imagined. And you knew you wouldn’t be going back after this. You were absolutely hooked on this man.

The build to your second orgasm was slow, but you knew it was going to be intense. Everything was getting warmer and harder to focus on anything but the pleasure that building. You clung to Dean harder, your needy moans being swallowed with kisses.

“Dean,” you breathed, your head buried into his neck, “I’m close. I’m so close...”

“I know, princess,” he murmured, running a hand through your hair. “Me too, me too.”

It was only moments later the two of you were coming together in pure bliss. Your mouths were mashed together in a slanted kiss, and you were trembling all over as waves of pleasure washed over you again and again. It took a few minutes for your breathing to finally even out and for you to gather enough strength to get dressed.

Dean groaned and tried to grab you to keep you next to him, but he missed by centimeters. “Noooo, come back.”

Grinning, you threw his shirt at him. “Get dressed, dummy. Sam will be back any minute now, and I need to pack up my stuff. Which, in case you forgot, is in the next room over. C’mon.”

Minutes later, when you were both dressed decently, you walked over to your motel room and swiped the key card through the slot. You opened the door only to see Matt standing there, half dressed with a not-so-happy expression. His eyes fell on your fingers that were linked with Dean’s.


	4. Good Morning - Sam Winchester

**Summary for the Chapter:**

> You wake Sam up in the morning with a blowjob.

**Notes for the Chapter:**

> This is definitely an oldie and unedited. Decided to keep it because I posted it on here before and it was quite a hit. People really seemed to like it, so.

The previous night, you were lucky. The moment your head touched the pillow, you passed out onto the motel bed, still dressed in the mud-covered clothes you were wearing during the hunt. You were lucky you had been dating Sam for a year, and he was around to take care of you when you fell asleep. 

You woke up in an oversized t-shirt ―which was Sammy's, as he liked seeing you in the morning with nothing but a pair of your panties and his shirt― and your red panties. A grin formed on your face as you sat up. Last night was a full night's sleep, you could tell. You didn't wake up in the early hours of the morning or with backaches from the hunt. 

You glanced at the door just to see Dean opening it. You raised an eyebrow, as if to ask, "Where you going?"

"Getting some breakfast and fueling up the tank before we leave," he explained, and left the motel. 

Minutes later, you could hear the sound of the Impala purring to life. You glanced at the sleeping body next to you, grinning slightly. Sammy looked too adorable sleeping with his arm hanging over his head and his mouth slightly open. 

With every intention of waking Sam up, you pulled the blankets off his body, only to see Sam wearing nothing but boxers. Those boxers, though, had a very large bulge in the shape of a tent. Your hand twitched, and your lower-half tingled. A sly grin made it's way to your lips. 

Sam always wanted to wake up to a blowjob in the morning, and no girlfriend of his had ever bothered to make that wish come true. Knowing Dean could take his sweet time with breakfast and fueling up the Impala's tank, you and Sam had a half hour at the most. That was enough time to make Sam come hard, and for you to at least start a shower. 

You didn't waste any time in starting. You hooked your fingers inside Sam's boxers and pulled them down, watching as his hard cock slapped against his stomach. You straddled Sam's legs, pinning them down as you took his cock in your hands. 

You swiped your tongue along his underside, causing a shudder to shake his body slightly. You grinned before you wrapped your lips around his hard and quivering member. You lowered your mouth down until Sam's cock made you gag. You brought your head back up and pushed it back down as soon as your lips reached the tip. You continued this for a few moments before you looked up to see Sam shifting, half-awake.

"Y/n?" he stutters as he glances down at you, surprised. 

You respond with your hand gently massaging his balls. Sam groaned, letting his head fall back on the pillow. You heard a few profanities leave his mouth as soon as you started pumping his cock with one of your hands. Sam reached one of his hands down and tangled them into your hair, tugging gently. It didn't take long for Sam to tell you he was close to coming. 

It was when you squeezed his cock gently as you pumped it and hallowed out your cheeks that you felt Sam squirt hot liquid down your throat. You swallowed every last drop. You rose from your spot and watched Sam's chest fall and rise, breathing heavily. 

You could only grin when Sam's eyes met your's. "Good morning, Sammy."

You left the bed, grabbing a pair of jeans and a shirt, and headed towards the shower, knowing fully well that Sam was watching you. Without a word, you locked the door behind you, and started the hot water.


	5. Tough Night - Sam Winchester

**Summary for the Chapter:**

> The brothers come back from a hunt worn out. For Sam, you've got the perfect solution.

You normally didn’t go on hunts. Being a long-time friend of the Winchesters meant you tagged on a lot of their hunts without doing anything to help them. Normally you just made runs for them when they needed it. And so when they found the bunker, you nearly cried with relief. No more tagging along on hunts.

So a little ritual started up - you’d stay at the bunker when they would go on hunts, do any research they needed, clean what they needed, and when they’d come back, you’d cook up a big meal for them. It was nice. You got to spoil your boys a little when they came back.

An annoying ringing noise sounded close. You patted the mattress blindly before the phone came in contact with your fingers. Without looking, you answered the phone and pressed it to your ear.

Groggily, you said, “Mmm, (Y/N) speaking. Who the hell is calling?”

There was a familiar chuckle and you sighed. “Oooh, someone’s cranky.”

“Stuff it, Dean. What do you want?”

“Sam, do you hear that? Do you hear the way she’s talkin’ to me? Rude!”

Your eyes still closed, you said, “I will hang up in five seconds if you don’t answer my question.”

“Fine, fine,” you heard him grumble. “We’re just calling to tell you we’re on our way home. Happy now?”

“Ecstatic,” you mumbled sarcastically before telling the boys to be safe. You hung up and tossed the phone aside before rubbing the sleep out of your eyes. Spending most of the day cleaning up the library after the amount of research you did the other day had exhausted you. So you laid down and took a nap. Only it was nearing seven o’clock and the boys were due home.

Wearing nothing more than a pair of leggings and one of the boys’ shirts, you made your way to the kitchen. You knew exactly what to make - teriyaki chicken with rice. It’s been awhile since you made it and it sounded good enough. Pulling out all the ingredients, you started your dinner.

You heard the footsteps of the brothers walking into the bunker just as you began to finish up the rice. Looking over your shoulder, you saw the pair of them looking pretty beaten. A few visible cuts and scrapes. Dean looked like he was limping. But Sam looked like he could barely stand on his feet.

“What in the hell…” you mumbled before handing them each a plate. Sternly, you told them, “Eat first. Then you can shower and relax. Fill your damn stomachs.”

Sam and Dean listened, knowing that you wouldn’t let them go anywhere unless they were fed. The sounds of forks clinking against glass was the only sound in the bunker, other than the small groans from the boys. You’d bet half of them were groans of pain and the other half was the good food.

But when the food was finally gone, you helped tend to Dean. His ankle was sprained - not broken thankfully - so you brought him to his room. You propped his ankle up and put an ice pack on it to help the swelling. After getting him a glass of water - and promised to stop babying him the rest of the evening because for the millionth time he was fine, he said - you left to check on Sam.

You hesitated at his door before knocking.

Sometimes you babied the boys and practically smothered them after hunts. You couldn’t help it. All you wanted was for them to be fine. The monsters and the cases scared you - that’s why you didn’t go on them.

Sighing, you knocked anyway. You’d worry your head off until you knew Sam was okay.

A small groan came from the other side, followed by: “come in.”

You peeked your head into the room to see Sam laying face down on his bed, wearing nothing but a pair of sweatpants. Closing the door behind you, you walked a little closer towards his bed. His back was full of scars, old and new. There were a couple by his shoulder you could tell was new - bright red and long. But his back was muscled and slightly wet from what was probably a shower.

“You look like hell,” you told him as you sat on the edge of his bed. “Need a massage?”

A massage was something you didn’t regularly offer. In fact, you’ve given them one only a couple times. But you knew Sam needed one. His body was sore and tense from the hunt. He groaned as you trailed your fingers down his spine before going back up to his shoulders, rubbing gently. But you didn’t get an approval  yet, so you pulled your hand away.

There was a muffled whine coming from Sam. It made the corners of your lips pull up into a smile as you said, “C’mon, Sam, I know you need one. Just say yes.”

He turned his head so his words wouldn’t be muffled. “Please and thank you.”

Patting his back lightly, you grinned before heading back into your room to grab the lotion. Dean was picky and wouldn’t let you massage his back with any of your girly smelling lotions. So you ended up getting an unscented lotion just for Dean and kept it around for instances like this. When you went back into his room, Sam was in the same position.

You climbed on the bed and straddled his legs. This position didn’t alarm Sam - you did it the few times before you massaged the boys’ backs. Plus it was easier this way. You squirted a fair bit of amount into your palms and rubbed them together to warm up the lotion. Then, you began the massage at the middle of his back, spreading the lotion all over his skin before really getting into it.

Keeping your pace slow, you rubbed your thumbs into the middle of his back. You knew that he preferred it a little firmer than Dean did. So the more you continued the massage, the firmer you rubbed into his skin.

The massage continued on for a while. Sometimes you’d hear a muffled noise coming from him, like a low grunt or a dragged out, damn near inaudible moan. The sounds he made were shot straight to your core. Often times you had to tell yourself to not get so into these massages. That you were only helping a friend and not your long-time crush.

You worked your way up towards his neck until you had to straddle his lower back. Working your thumbs into the crook of his neck, you could feel how tense he’d been. You sighed, shaking your head.

“Damn. What did you do on this hunt, Sammy? You’re so tense,” you said.

“Flipped on my back a couple times,” his low mumbled reply came. “Tossed down a hill. My body just hates me, I guess.”

His words struck something within you and before you could think twice about your actions, you leaned down and pressed a lingering kiss on his shoulder. You repeated this twice along his shoulder blade and then again on his shoulder. Leaning against him, you continued with your massage.

“What’re you doing, (Y/N)?” he asked.

You were throwing caution to the wind. If you weren’t going to do this now, you never would. This was your chance and you were taking it.

“Showing your body love since it hates you so much,” you whispered low enough for him to hear. Then, at last minute, added, “Let me know if you want me to stop.”

Pulling your hands away from his neck, you ran your fingers down his back in mindless patterns as you pressed kisses against his shoulder blades. You went from the left side to the right, some lingering longer than the others. Leading up to his neck, your kisses went softer and softer until they were barely brushing against his skin.

You could hear Sam’s breathing become heavier as your kisses became gentler. He was anticipating each kiss, waiting for your next move. And he hadn’t said a word.

Daring yourself, you moved up his neck to his jawline. Then without warning you nipped at the skin of his jawline, inches below his lips before pulling away. You were smirking, feeling quite smug after that. So you didn’t expect to Sam turn over under you. You were no longer straddling his lower back but his lap. Your eyes widened as he sat up, your faces inches apart.

“You gotta tell me if you wanna back out,” he murmured.

His breath tickled your mouth. That’s how close you two were, breathing in each other’s exhale. You were dazed as your body was filled with desire and delight. This was happening. Whatever this was, it was finally happening. No more fantasies.

So you closed the gap between you two. Cupping his cheeks, you pulled yourself to his mouth as you kissed him. His lips were soft as they meshed with yours, his fingers digging into your hips. It was a series of slow, testing kisses, seeing how far you both were willing to go.

It was when Sam capture your lip between his teeth you started to grind down on his lap slowly. Then, a low groan escaped his mouth. You couldn’t help but smirk a little as you ground yourself down against his lap in a slow, teasing rhythm. Sam’s fingers tightened on your hips, spurring you on.

As you ground yourself against his lap, you felt his fingers rise from your hips. His fingers tickled as they skirted your ribs. Though your kissing has been resumed, it was sloppy. Your focus wasn’t on his lips but how good he felt underneath you, his hard length straining against his sweatpants. And his fingers and where they were headed…

Sam lifted your shirt over your head, leaving you in your black and white polka-dotted bra. For a moment, his eyes flickered down and as he sucked in his bottom lip, appreciating your chest. Just as you were about to start grinding against him again, he immediately flipped you both over. Now you were underneath and he was hovering above you with a grin.

Breathless, one of his hands trailed along your sides and hip. His fingers were light as they traveled across your skin, never quite finding a perfect spot. That was until you felt his hands on your inner thigh. A whimper escaped you when you realized just where he was heading.

But just as his fingers skirted along the lining of your panties, he pulled his hands away. Whimpering, you bucked your hips against him, hoping he’d get the hint. But he never let up, teasing you. His fingers always found a spot and fingered the lining of your panties, never quite going in.

“Sam,” you groaned, bucking your hips again. “Please.”

A low chuckle passed his lips as his hand slipped underneath the waistband of your panties. The pad of his fingers found your bundle of nerves, circling the bud a couple before he slipped his index and middle finger into your folds. The moan that left your mouth was loud.

Immediately his mouth was on yours, shushing you. But his fingers never stopped. He pushed them deeper into you, searching for that one spot. Your hands gripped onto his shoulders, moans muffled as lips clashed together. When Sam’s fingers brushed against that spot, though, your hips bucked against his hand.

A smile grew against his lips. His steady rhythm was changed into a fast-paced rhythm as he curled his fingers. You were already climbing high towards your orgasm, but when he began leaving marks all over your collarbones and neck, you were done for. You were a moaning mess, whimpering his name as you clutched onto his shoulders all the while leaving marks. Then, Sam brushed his thumb over your clit a few times.

It was like a rubber band snapping. You were being stretched and stretched until finally you couldn’t take no more. You cried out Sam’s name as he worked you through your orgasm.

Sam pressed small kisses to your lips as you tried to catch your breath. The kisses moved to the corner of your mouth, your jaw line up your temple, and then finally your forehead.

You grinned up at him. “Not done with you yet, Sammy.”

Immediately, you pushed him off you and discarded the rest of your clothing. Wasting no time, you straddled him and hooked your fingers into the band of his sweats, tugging them down. His hard length slapped against his bare stomach, and you had to bite your lip.

Fuck, he was perfect.

You took him in his hands, stroking him a few times before lining him up at his entrance. As you sank down, your eyes flickered to meet Sam’s. His brown hair was a disheveled mess, his bottom lip trapped between his teeth and his pupil-blown eyes were watching your every move.

He looked big but he felt bigger. Once he was fully inside you, you had to wait and adjust to his size. Sam’s hands found your hips. The man was patient as you waited until you were finally ready.

And when you were, you rolled your hips slowly at first. A groan tumbled from Sam’s lips as you began moving, finally getting the hang of it. Your hands rested on his torso, fingers curling tightly. Throwing your head back and moaning, you attempt to keep up the pace. But your rhythm is getting sloppy and you can’t help yourself.

Sam sat up, pressing his entire chest against you as his hands grip onto your hips. He guided your hips up and down his cock as you gripped onto his shoulders tightly. With this new position, you had to wrap your legs around his waist to get comfortable. But oh god, did it feel just as good.

It could have been minutes or hours that passed. You weren’t sure how long it was, but all you knew was how good Sam felt. How good everything felt. His cock thrusting into you. One hand on your hip, the other tangled in your tousled locks. Your bodies pressed completely together as you panted, nearly inaudible moans escaping your lips including the occasional ‘fuck’.

But that coil began to tighten and you could barely focus on anything that wasn’t Sam. Your fingers tightened in his hair as your orgasm neared, whimpering out Sam’s name.

“C’mon baby,” he said, his voice low and rough. “Come for me.”

And you came.

Your body trembled and shook as you locked yourself around Sam, burying your face in the crook of his neck until your it’d passed. For a moment, you didn’t move.

For a long time, you’d longed for this. Dreamed about it, even. You were in love with Sam and though you wanted it so badly, you also dreaded it. What would happen now? Was it a one-time thing? Your chest tightened painfully at the thought. You couldn’t handle going back to being friends after this. You cared for the hunter too much for that.

Untangling yourself from Sam, you didn’t look at him as you started to pick up pieces of your clothing. You were just starting to pull your shirt over your head when you felt his hand on your arm.

“(Y/N), what are you doing?” he said, his voice low and quiet.

Your words died in your throat as you dared to look up at him. What were you supposed to say? That you fell for the man and wanted nothing more than to climb back in bed with him? That you’ve wanted to fuck him for a long time now? That you loved every single second of sex with him? Nothing. You were supposed to say nothing.

When you said nothing, he spoke up again. “Please… please don’t tell me this was a one time thing, (Y/N), because I don’t think I could handle that.”

You croaked, “What?”

“I’m in love with you,” he said as he gazed down at you with those eyes. Those eyes that you loved… “Have been for a while, actually.”

You dropped everything in your arms as you cupped his cheeks and pulled him down for a searing kiss. Your heart was soaring and butterflies were erupting in your stomach. And all you could do was clutch onto Sam and kiss the hell out of him.

Out of breath, you pulled away panting. In between breaths, you told him, “I love you, too.”

Half dressed, the both of you climbed back into bed. Sam pulled the blankets along with him and covered the two of you as he wrapped his arms around you. Everything was soft and warm, you couldn’t help but doze off immediately.

When you woke up from your deep slumber, Sam’s arm was curled around your waist, keeping you tight against his warm chest. You stifled a giggle as you pried yourself out of his grip. He stayed put, thankfully, and without waking up. 

Sex after a tough hunt probably wasn’t the best idea for him. Even with the massage. The guy was probably worn out. 

Leaving Sam to sleep, you tiptoed quietly to your room so you could get dressed. Choosing a pair of leggings and a long-sleeved shirt, you piled your hair on top of your head before leaving your room. 

When you got to the kitchen, you saw Dean sitting at the table with a plate of breakfast in front of him. He eyed you for a moment before his face lit up and grinned at you. 

“Sleep well, (Y/N)?”

You raised an eyebrow. “Yes, just fine…”

Odd…

You tried to ignore Dean as you started a pot of coffee. Moving around the kitchen, you grabbed your mug and began making your own breakfast. Dean kept sending you small smiles every now and then. And though you returned the smiles, you thought he was acting a little weird. Dean wasn’t normally like this, especially in the mornings. 

You finished making a cup of coffee and your breakfast just as Sam walked into the kitchen - shirtless. You didn’t make eye contact. Instead you dived right into your breakfast. It was when Sam finally sat down and you took a sip of your coffee that Dean said something.

“Those are some really nice hickies (Y/N) has, right, Sam?”

Your coffee spewed everywhere on the floor. You looked up at Dean with wide eyes. He had a mischievous glint to his eyes and the corner of his mouth was tilted upwards into a slight smirk.


	6. Tease - Dean Winchester

**Summary for the Chapter:**

> It's a hot day and you take the opportunity to tease Dean.

It was one of the warmest days of the summer and  _ god _ , you felt like you were burning alive. The three of you – you, Sam, and Dean – were all lying in a motel with a broken air conditioner. Every window was propped open and even the screen door to the motel was open. You had a pair of spandex shorts and a sports bra, but even so it felt like it just making it worse. Your body was drenched in sweat and it was just  _ so fucking hot _ .

Sam immediately stood up and pulled on a light shirt before snatching the keys. You quirked an eyebrow at him. “Where are you going?”

“I'm going to find a motel with working air conditioner – screw this,” he said. And without another word from either of you, Sam headed outside in the blistering sun.

You glanced at Dean. He seemed to not care about Sam or the fact that he was driving his car. Biting your lip, you stood up too and grabbed a pair of flip-flops and a credit card. Earlier you'd already pulled your hair into a tight bun to get the hair of your neck so you didn't need to do anything with it – you were planning on going out in what you're dressed. The weather was too ridiculous to go in anything else.

As you moved toward the door Dean looked at you. “And where are  _ you  _ heading, huh, [Y/N]?”

“Getting something cold to eat or drink. Want anything?”

“Yeah. Get me something to drink.”

There was a gas station down the street from the motel, close enough that you could get something to drink and be back before the heat fried your brains. It was just as hot as you thought it'd be the moment you stepped outside. The air hot, the sun felt like a match getting ready to light everything on fire, and you were burning.

But the idea of having something cold in your hands and in your mouth was enough to push you forward. You got glances and men were rude but you ignored them. It was far too hot to wear anything else. But you arrived at the gas station within five minutes. There was a burst of cold air and you sighed happily. At least this building's AC worked wonderfully.

You decided a box of popsicles and a few ice cold drinks would be fine – as long it was cold, it would be more than fine. At the counter, the girl saw your attire and flashed you a smile.

“God if it got any hotter, the earth would light up in flames,” she joked.

“It doesn't help the AC is broken at the motel. Next best thing,” you laughed motioning to the cold items on the counter. One by one she swiped them and set them into a bag.

She winced. “Oooh. Well shit, that sucks.”

You nodded as you swiped the credit card. “My friend left to go check into another motel. Way too hot for sitting in a motel with a broken AC.”

“Yeah I don't blame you,” the cashier said, handing you the plastic bag of goods. “Have a nice day.”

With a nod of your head, you unwillingly left the cold gas station and back into the heat. Your feet moved fast, flip-flops slapping against the pavement with each footstep like a constant rhythm. Beads of sweat ran down your temple, hitting your collar bones and running down the valley of your breasts. You moved fast, ended up sweating more, but got to the motel room quicker.

You panted as you shoved the door open and threw a soda in Dean's direction. Wordlessly you took out the box of popsicles and took one out, throwing the rest into the freezer. They were bright red and cherry flavored. Unwrapping one you popped it into your mouth, moaning in the process. The cold treat against your tongue felt so wonderful.

You nearly devoured the popsicle, switching between small kitten licks and wrapping your mouth around it. So caught up with your popsicle, you didn't notice that you had captured someone's attention – until there was a small groan coming from the other side of the room.

Your eyes lifted and met Dean's gaze.

Slowly you lifted the popsicle to your mouth and sucked on the very tip of it while never looking away from Dean. The intense look he gave you in return was enough to heat your body. It wasn't a bad type of fire that ran through you, it was one of the best. Very subtly, you clenched your thighs together while hoping it didn't catch his attention.

By the slow smirk,  you knew that it did. You needed to redeem yourself and quick. So you brought the cold popsicle further into your mouth and hallowed your cheeks as you pulled it out again. You repeated the process a couple more times while never letting the popsicle fully leave your mouth.

The smirk on his face never really left until you ran your tongue from the bottom to the tip of the popsicle very slowly. There was almost a challenging look on your face as you did this, watching as the smug look on his face vanished.

You spoke while trying to hide your smile. “Can I help you, Dean?”

He didn't respond – he was too busy watching as a drop from the melting popsicle fell onto your collarbone and slowly dripped between the valley of your breasts. His tongue poked out and ran across his bottom lip before he caught his bottom lip between his teeth. The heat flared again, the smile dropping from your face and your popsicle all but forgotten.

“I don't know, maybe–”

Whatever Dean was about to say was cut off as the screen door of the motel was wrenched open, revealing Sam with a huge grin.

“Good news guys. There's a motel across down and they have an opening with a working AC. Even better – they have a pool. Let's pack up and get the hell out of here, I need to cool down.”

Dropping the popsicle in the sink you washed off your hands and you began to pack up your things. Dean did the same, both brothers falling into conversation about the case you came here for, making plans for tonight. You weren't even listening.

You were distracted by thoughts of whatever Dean was about to say and hoped that maybe he was about to make a move. You could only hope that he'd try again…


	7. Feathers & Blindfolds - Dean Winchester

**Summary for the Chapter:**

> Dean decides to spice it up a little in the bedroom and to surprise you at the same time.

**Notes for the Chapter:**

> Chapter warnings: blindfolds, being tied up

The moment Sam retired to his bedroom for the night was when Dean rose from his chair at the table and walked around until he was behind you, hands on your shoulders and slowly pushing back your jacket. His fingers dug into your skin, massaging your shoulders. 

Your eyes fluttered shut as your head hung low, letting Dean do as he pleased. “What are you doing?” you murmured.

His lips pressed against your neck gently. “I want to try something new. You up for it?”

God, he was talented with his hands... his lips... you couldn’t say no. Nodding your head, Dean pulled away and kissed your neck one more time before saying, “Good. Then go to your room and get ready. I put something on the bed for you. Meet me in my room in ten minutes.”

And then, Dean was gone, disappearing to his room.

You stared for a moment. Sex with Dean was amazing -- which was why you two were doing things behind closed doors and without Sam knowing (it was something you both agreed he did not need to know; TMI for that hunter for sure). But when he said he had something new he wanted to try, you couldn’t help but feel tingles and excitement all over. 

So you got up and went to your room, opening the bedroom door. Just like he promised, there was a little black gift bag sitting on your bed. Biting your lip, you moved towards it, curiosity pushing you forward. What exactly did he buy?

You peeked inside and immediately, you were beet red. Lace. The kind of lace you wore for a specific reason. Hesitantly, you pulled the garments out and blushed even more. Dean bought you a black sheer lace bra and panty set. Fingering the material softly between your thumb and index finger, it was soft. 

You looked down at the gift bag realizing there was a handwritten note. In Dean’s scrawl, it read, “Put this on and then come to my room.”

For a few moments, you stared at the sheer fabric in your hands. It was sexy and definitely had promises of a night filled with sweat and moans and all things perfect. But your curiosity was burning bright. What exactly did Dean have planned? So you did as he told you, first stepping inside the bathroom to clean up a little. It was a long day and you preferred to be clean - despite the fact that you’d be getting dirty later...

Fifteen minutes later, you stood in front Dean’s bedroom door with a silk robe wrapped around you. Underneath was the sheer lace bra and panty set Dean bought for you. Your hand rose and you knocked lightly. There was movement on the other side of the door, but just as you thought he’d open the door something slid underneath the crack of the door. 

Glancing down, you narrowed your eyes as you picked it up gently. Your eyes widened when you realized it was black fabric. There was a small note taped to it, reading: ‘ _ blindfold yourself & knock again _ ’. 

Gulping, you tore off the note and balled it up in your hands before tying it tightly around your eyes. Then, just as instructed, you knocked on the door. It opened within seconds and familiar hands pulled you forward.

The loss of sight kept you unfamiliar with where you were at - but you knew by the warm hand enclosed around your wrist that you were going to be okay. If Dean had plans with blindfolding you while wearing lingerie, you knew he was going to keep you safe.

“Remember what we talked about a while ago -- about what you’re comfortable with?” his words were just a whisper, but they brought back memories of a discussion.

After the first few times Dean and you were together, you had set boundaries and limitations, things you were comfortable with and things you weren’t okay with. Dean remembered very well your limitations. 

You nodded your head slowly, your hand searching for some part of him. You relaxed slightly when your hand found itself resting on his bicep. 

“Do you remember what you said about being tied up?” Again, you nodded. “Wanna repeat your words for me?”

With a shuddering breathe, you spoke the words he was looking for. “I-I’ll agree to it and go along with it so long as I’m not tied up with rope or handcuffs -- and it can’t be too tight.” 

“Good girl.”

And then, Dean began to lead you, pulling you along. You followed blindly with slow steps until he started pushing you down. Below you, you felt the soft comfort of a bed and the sheets on it. Dean helped you situate yourself, sliding off the silk robe - there was a sharp intake of breath from him that made you want to grin - and position yourself. Before he tied you to the bed, he took your hands and put a soft, silk-like fabric in them. You felt the fabric, turning it over and feeling the silky softness before realizing it was a tie -  _ his  _ tie.

A shaky breath left your lips as you nodded your approval. Both wrists were tied after you were laid down. Just like you requested, it wasn’t that tight. You were restrained, of course, but you could still move your wrists a little and even escape if you so desired it.

For a moment there was nothing but silence. Now that you were on the bed and restrained, you couldn’t tell where Dean was. He wasn’t on the bed, you could have felt if he was. 

“You remember the color system?” he spoke, his voice coming from the end of the bed. When you nodded your head quickly, he continued speaking. “Tell me the colors and where you’re at right now.”

“Green for go, yellow for slow down and red for stop,” you breathed and then after a moment, said, “Green. I’m green.”

Moments later, there was dip on the side of the bed. He didn’t say anything for a moment, though you felt his gaze on you. You breathed heavily, waiting in anticipation, for something to happen - anything, really. Just as you were about to open your mouth to beg Dean to do something, something soft trailed along your calf. 

Gasping and jumping in surprise, you heard a low, throaty chuckle as the same sensation appeared in the same spot. You expected it this time so you relaxed, giving into the sensation. You didn’t know what it was but it was soft and somehow erotic at the same time.

Your breathing slowed, the trailing of the soft sensation going from your calf, to your feet and toes. You weren’t able to help sighing as your body completely relaxed. Whatever Dean held in his hands was soft and sort of ticklish as he ran it slowly up your calf again, rising higher than your knee and trailing it in patterns on your thigh.

There was a hitch in your throat when he began to raise the soft object higher, twirling it in circles. Your skin had become sensitive and you were all too aware of how goosebumps raised on your skin where the soft object trailed. Automatically you yanked on your restraints when the soft object started going in circles on your hip, right along the waistline of the panties you wore. 

Another throaty chuckle. “Patience, baby.”

The soft object - which was beginning to feel like a feather, now that you thought about it - was moved from your hip to the skin right behind your ear. You gasped as the feather trailed delicately from your ear, along your jaw, to the bottom of your lip, the other side of your jaw, to the soft skin behind your ear and back the way it came. A soft sigh left your lips. This was unlike anything you’d ever felt. You were practically numb with ecstasy, awaiting the next place the feather would go... 

A moan was wrenched from you when the feather trailed delicately down your neck, across your collar bones and tickled along your side. Dean kept repeating the trail he just made. How a feather, so soft and light, could make you want so badly for Dean’s warms hands on your skin, you didn’t know. His teasing continued. All you wanted was to toss that feather aside and have his hands roam across your body. 

The feather skirted across your ribs, right underneath the lining of the bra... Up and down your side again, traveling across your arm where Dean tickled your palm... 

It continued forever like that, the feather traveling gently over your body, in teasing places like the curve of your breasts and below the lining of the bra, the waistline of your panties, and the inside of your thighs - that was worst place. Because it was so dangerously close to your center and you were nearly fed up with Dean’s teasing feather. No matter the amount of moans or whimpers that escaped you, he wouldn’t let up.

Until...

“Fuck!” you cried out when he left the area of your thighs. You were done with the teasing, finally hitting the limit. “Dean, please. Please, please, please, no more teasing. Want you.. Need you.. So bad...”

The feather disappeared and you sighed with relief. There was a sound of clothes shuffling and then another dip in the bed. Dean straddled you, hands on either side of your head. 

“You ready, baby?” his voice was at your ear and the only answer you could give him was a quiet whimper.

Then, his lips attached themselves to yours and your lips moved together, eager to feel warmth and lips instead of the soft, delicate feather. While one hand stayed planted on the bed to support his weight, Dean’s other hand traveled along your arm and moved lower, lower, and lower until it rested comfortably on your hip.

You moaned, bucking your hips into his. “Dean, please.”

He pressed a light kiss to your jaw once, twice, and again before he sat up. Moving aside, he tucked his fingers into the waistline of your panties and tugged them down, throwing them aside. Neither of you cared where exactly it landed. 

Then, he lifted your leg so it was resting on his shoulder, leaving you open and bare to him with his erection pressing against you. And then, he pushed his hips forward, slowly thrusting into you. Dean let out a barely audible groan while your breathing hitched in your throat, a soft moan escaping.

As his thrusts were slow - slowly quickening in pace - you tried to push against your restraints. If you were tied up, without the eroticness of it all, you could have found a way out within seconds. But now, your head was clouded with pleasure, with the heavy breaths coming from Dean, and how good he felt inside of you. You pulled against the restraints anyway, whining when you weren’t able to touch him. 

It wasn’t long before Dean let your leg fall and pulled out for a moment. Just as you were about to protest, you felt him lean in and begin to untie both hands, freeing them. And then before he could blink, you had switched positions with him. He was beneath you and you had lined yourself up against his hard length. You entwined your fingers with his, blindly, and sunk down.

He groaned beneath you but you kept up a steady pace, nothing too slow but nothing fast either. You were ecstatic now that your hands were free... You pulled your hands away from him and felt his bare skin, your hands trailing from his biceps to his shoulders and down his chest where your hands rested on his lower torso. All the while, you heard his heavy pants and the quiet groans mixed in.

All the while, you never bothered to remove the blindfold. It was... A whole other sense not seeing things. Without your sight, you focused even more on touch and how Dean felt. It was like without your sight, your sense of touch was heightened. You didn’t mind it either - it was erotic and sexy and just about one of the best ideas Dean has ever had.

You felt, though, when he was getting close. And you weren’t far behind him. So you pushed yourself to quicken the pace, ride him harder. His groans were louder and so were your sounds. One hand moved from his torso to your clit. With just a few finger-strokes and you were gone, eyes shut and falling blissfully...

Dean wasn’t that far off from you. Actually, just as you finished your orgasm, Dean began coming with a shout of your name, hips bucking upwards sloppily. When you were both finished from your high, you had gotten up to clean yourself off in the nearest bathroom right after you undid the blindfold.

When you got back, you unhooked the bra and let it slide to the floor before picking up a shirt off the floor. It was the exact same one Dean wore earlier today. You slid it on. It fell just below the curve of your ass, but you crawled in his bed and curled up next to him.

Dean wrapped an arm around you, placing a soft kiss on your temple before pulling up the blankets to cover you both. When you looked up at him, his eyes were already shut but a lazy smirk was playing on his lips.

Feathers and blindfolds... So much fun.


	8. First Time - Castiel

**Summary for the Chapter:**

> Cas asks for help with a particular human issue the reader might know about.

Being the little sister of two hunters—the Winchesters, no less—was a pain in the ass. Despite the fact that you knew just as much as them and could kick ass just as well, if not better, you were still treated like a child. It pissed you off more than you could say. All you wanted was to help out Dean and Sam, but nooo. You were a child in their eyes and were forced to stay back at the motel while they worked on the case.

At least you weren’t alone, though. Cas has been distracted a lot recently and instead of going with the two brothers had decided on his own to hang back.

He was sitting on the edge of one of the two beds in your motel room, hands folded in his lap and his head hanging down with his eyes trained on his hands. You could see from where you were sitting that something had to be bothering him. Knowing you weren’t going to do anything else the rest of the night, you got up from your spot on the bed and plopped yourself down next to Cas.

You startled him, his gaze meeting yours. Putting a hand on his knee, you asked, “Are you all right, Cas? Something bothering you? You can always talk to me, you know. I may be a hunter, but I’m a pretty good listener, too.”

Cas pursed his lips, his gaze flickering between his hands in his lap and your face. You could see how his thought process was on his face, wondering if it was all right to reach out to you. When he sighed, his shoulders slumping slightly.

“I… Sex… between humans… how does… how would that work?” he asked, his blue eyes all innocent as he looked at you.

Immediately your face heated up and turned a vivid shade of red. Sure, you’re not all innocent as your brothers believed and you weren’t a virgin by any means—but to discuss this with an angel was… it was nothing you’d ever expected.

“I… well,” you struggled with your words, racking your brain for something to tell him. “It’s usually between two people who like or really care for each other… um… Why would you ask this, Cas?”

Pink bloomed across his face as he stuttered out an answer. “My, uh… my, um, vessel…”

There was a sharp intake of air as you realized what was going on. Of course, his vessel was human and humans are controlled a lot by their hormones. Sex, sex, sex. Cas fell silent as he knew that you’d caught on. For a moment, you could only stare and bite your lip.

And then you spoke, your cheeks still red. “Do you want me to show you? It’s easier to show you what it’s like. You don’t have to…”

Your words trailed off when Cas nodded his head. Taking in a deep breath you turned your entire body so that you faced Cas. Oh, if anyone found out about what you were going to do—especially your brothers—you were going to be in deep shit.

“Normally it starts off kind of like this,” your words fell into a whisper as you nudged yourself closer to Cas. You placed a hand on his neck, pulling him closer. Cas seemed to understand what you were doing so far and didn’t fight it. Your lips were hovering over his, just close enough that one simple move and you two would be kissing.

You leaned forward and pressed your lips against Cas’ before you could talk yourself out of doing this. His lips were soft and gentle as you kissed him and he kissed back, easily following your movements. Using your only free hand, you grabbed one of his hands and placed it on your waist.

And then while the kisses never stopped, Cas began pulling you down onto the bed until you were both laying down. The kisses became deeper, more tongue and teeth, as your body heated up. Then, you placed your hand on top of Cas’ and guided his hand further up your waist and underneath your shirt.

When his fingers brushed against your bare skin, his grip on you tightening just slightly, you let out a soft sigh. It wasn’t long before you felt his hard length against your thigh. Cas pulled away, flushing and panting.

“Yeah,” you managed to whisper, your eyes falling shut. “That’s how it starts. Would you... would you like me to show you more? Or what are you comfortable with?”

It was a long moment before he responded. You opened your eyes, seeing Cas bite and chew on his bottom lip as his blue eyes were on you. Your hand came up and gently cupped his cheek. Releasing his bottom lip from his teeth, you traced it with your thumb. His bottom lip was red and swollen from the previous kisses.

When he spoke, his words were so quiet you had to really listen to hear him. “Could you show me... everything?”

Suddenly it was hard to breathe, hard to focus on anything but the angel in front of you. His words were swimming around in your mind and you were sure you wanted nothing more than the angel in front of you.

“Everything?” you whispered.

“Everything,” he repeated.

Then you were pulling him to you, kissing him with everything you had. His hands found your hips again, slipping underneath the shirt you wore. Your hands than drifted from his face to his black blazer, slowly tugging it past his shoulders and down his arms.

There was only a brief pause in kissing to discard his blazer and to straddle his hips Then you were right back where you left off, undoing his tie and tossing it aside. Your fingers deftly undoing each button until his bare chest was revealed. When you ran your hands across his chest in random patterns, a soft pleasured sigh escaped him.

You pulled away, pressing small kisses down his jaw and neck. His breathing increased, his bottom lip trapped between his teeth. God, what a sight was he.

“You look wonderful, Cas,” you whispered as you lowered yourself between his legs.

His eyes were glued to you, watching your movements with curiosity and wondering what exactly you were going to do. You began to unbutton and unzip his pants, ordering him to lift up his hips. When he does you tug down his pants and his boxers along with them, his cock springing free.

Your eyes not tearing from his, you lick a bold stripe on your palm before you wrap your hand around his cock. Cas’ eyes widen as he moans. You can tell that he hasn’t even touched himself like this before, that this was brand new. The corners of your lips curl up when your hand keeps a steady pace.

“Does that feel good, Cas?” you ask him after a moment. His blue eyes find yours and he nods his head. “No, tell me. In words.”

“Y-yes,” he stammered when you began pressing small kisses to the tip of his cock, spreading precum all over your lips and his cock. “Oh my... it feels so good, [y/n]. Your mouth feels so goo— _ oooood _ .”

His last word turned into a moan, because as he was speaking you leaned down and wrapped your lips around his hard and waiting length. Slowly, you leaned down until the tip of his cock hit the back of your throat. Then back up. Down until you gagged and back up. Down, up. Your eyes were on him as you repeated this process, watching him as he fell apart.

His dark hair was tussled, eyes shut and mouth open in pure bliss. The sounds that were escaping this man... this angel... had turned you on and pushed you forward. Watching him moan and clench the sheets was enough to get you to sneak a hand into your jeans, pushing past your underwear.

Hell, you were soaked. Your finger circled your clit as you moaned around Cas’ cock, pulling away and using your free hand to pump him. His eyes found yours and glanced down to see why you had pulled away. You panted as he continued to watch you get yourself off.

A soft whimper left Cas and his head fell back again. You could feel his body tensing up and immediately, you pulled away. Suddenly, he was sitting up, worried that maybe you had changed your mind.

But you had only gotten off the bed to strip yourself of your clothing. Cas’ eyes were glued to your body as you brought the shirt over your head and unsnapped your bra. It fell to the floor as your nipples hardened from the cold air. And then slowly, your thumbs dug into the waistline of your pants as you tugged them down, leaving you bare.

“Are you ready?” you asked softly, straddling his hips again.

Cas was leaning back on his elbows as he looked up at you, nodding his head. So you kissed him lightly as you raised your hips, lining yourself up with his cock in your hand. His eyes fluttered shut as you sunk down onto his length, both moaning in unison.

Cas fell back his hands gripping your hips tight as you rocked against him, setting a slow pace. You whimpered when his hips started thrusting up to meet yours, both of you moving in sync, both moaning and falling apart. The fire in your core built slowly and slowly, a sheen of sweat appearing as you became closer and closer to an orgasm.

Both of you were sticky, the room smelling of sweat and sex, but you loved it. Hearing the sounds of Cas’ panting and pleas, your moans when you rocked against his hips faster and faster.

In a burst, you were coming, crying out Cas’ name over and over again. Just as you began to come, Cas followed you shortly after. Your name left his lips with a grunt as his thrusting hips became sloppy. Pressing a small kiss against Cas’ lips, you slipped out as he began to soften and crashed next to him.

A grin stretched your cheeks as you glanced at Cas. “So that’s how humans have sex.”

“Do you think that we could do that again sometime?” he asked, turning so his entire body faced you. “That was... better, a lot better, than I thought it would be.”

You couldn’t help but laugh as you curled against him, grinning as you kissed his chest a few times before answering. “Of course we can do that again. Anytime you want, as many times you want.”

Cas started to smile before it vanished, paling considerably. He looked down at you with a worried expression. “Do we have to tell Sam and Dean? Because I don’t think...”

You snorted. “Yeah, I think it’s best if we don’t tell Sam and Dean.... We can keep this just between us.”


	9. Little Black Dress and Grind (part 1) - Crowley

**Summary for the Chapter:**

> Reader and her friend Daisy are hunting down a particular demon. When Y/N is given the task of 'seducing' the demon, it does not end like she plans.

**Notes for the Chapter:**

> On Tumblr this was part of a follower celebration and this was one of the few I happened to like. Second part to come.

Sighing you tugged down on the hem of the dress, hoping that it’d grow an inch or two. You growled underneath your breath and cursed your best friend. You loved her dearly but you were way out of your comfort zone wearing this dress. Crossing spaghetti straps, a plain black color, and paired with decent four-inch heels. Your hair was styled to your liking along with make-up that accentuated your features. As you looked yourself over in the mirror, you cursed again.

Your best friend was definitely trying to kill you.

It was when you attempted to tug down on the dress for the fifth time that your best friend, Daisy, slapped your hand away and growled - yes, _growled_ \- at you.

“Stop it! The dress is fine you’re just overreacting,” she said as she rolled her eyes.

“But Daisy,” you tried to argue your way out of this again. “Why me? I’m just as capable to do your part. You’re way better at this than me. I’m going to fuck up!”

“You’re terrible at being bait _because_ you never do this,” Daisy said this as if it were the most obvious thing in the world. “You’re gonna be bait more often and you’re gonna learn how to do it well. Now stop whining and let's go.”

Groaning, you let your head drop and followed Daisy out of the motel, carrying nothing but a little clutch with a few emergency items. Like cash for instance and a few necessary hunting items.

For the last few weeks, a demon has been going to a club nearby. A few deaths occurred and that’s when you and Daisy decided to step in. All you had to go on was a few descriptions of him.

Average height, slightly round, middle-aged and dark-haired. That was all anyone described him as. Nothing more, nothing less. It could have been anyone but at least you had some sort of description... it wasn’t like you were going in _completely_ blind.

Daisy had to park a couple blocks away but made camp in an alley not too far from the club. It was where ‘it’ would happen. You’d drag the demon out of the club after seducing him, claim you want to go somewhere more private, then Daisy would climb out of the shadows and jump him. It was the best plan you could come up with for two tiny girls.

After promising to be out in a couple hours at the latest, you stood in line with everyone else. It wasn’t long before you were allowed inside with a stamp on your hand.  

Lights flashed, music pounded and vibrated enough that you felt it through the floors, and the smell of sweat and alcohol filled your nose.You covered your mouth as you tried not to gag. There was a reason you weren’t the bait besides the fact that you were terrible at it.

You couldn’t fucking stand night clubs.

Slipping into a seat at the bar, you ordered a simple jack and coke. If you were planning to be bait, you might as well drink. Taking your time with the drink, you let yourself slowly relax as you glanced around the room while searching for the demon.

Dark hair, slightly round.. Middle aged...

You sighed as you finished scanning the room. No one here matched that description. You thought it might have been a little easier considering everyone here was young. Anyone middle-aged would have stood out.

Just as you finished your drink, you motioned the bartender for another one. It was when he slid it to you that you noticed a new presence in the stool beside you. Lips curling into a smirk, you turned to face them only to have that smirk completely wiped from your face.

_Holy shit._

It was the demon. No doubt it was a match. But they didn’t say how charmingly attractive he’d be, especially with that scruff. You weren’t usually attracted to the scruffy sort but... there was something about the way he pulled it off. Maybe it had something to do with the dark suit and silk tie...

“Can I help you?” you raised an eyebrow.

When he spoke, you felt your stomach drop.

“Well, love, I noticed you looked a little irritated and wondered if I could be of any use,” he said, his voice thick with a British accent.

Oh, you were goner. The moment words started to spew from those lips you knew you were in trouble. You barely said five words to the man and you’ve already managed to fuck up this whole thing. It wouldn’t have happened if Daisy were here in your place instead.

“My friend was supposed to meet me here and she hasn’t shown,” you said, making sure to bat your eyelashes as you let your fingers skim the rim of your glass. “I’m beginning to think she won’t show up at all.”

“Then I hope you don’t mind if I join you,” he said, lips curling into a small smile.

“‘Course not.”

* * *

 

Two drinks later, you were practically putty into the demon’s hands. It wasn’t the way it was supposed to work out. It should have been the other way around, but you couldn’t fucking help yourself. He was so... _charming_ and fucking nice to you! He was a gentleman, no doubt about it, but he also had a lot of sass and wit that had you grinning. To top it all off, he could make you laugh without even trying. You constantly had to remind yourself that he was a demon, and you couldn’t let yourself be attracted to him.

Shoving the alcohol away from you, you abruptly stood from your seat and headed towards the dance floor. Glancing behind you, you smirked as you saw Crowley’s gaze on your behind.

“Comin’, mister?”

His teeth latched onto his bottom lip as he let his gaze wash over you before he stood from his seat. The demon followed you to the dance floor and stood behind you, your ass pressed against him. Pounding, vibrating music moved you as he set his hands on your hips, keeping you pressed against his growing erection. Lips brushed against your earlobe, nipping slightly, and moved lower, kissing and sucking at the skin of your neck.

Your moan wasn’t loud enough for anyone else to hear but him. He squeezed your hips as you began shamelessly grinding against him. He was rock hard in those trousers of his, and you couldn’t help but feel smug. That was _your_ doing. No one else’s. _You_ were the one that got him rock hard with just a swish of your hips.

He twirled you around and lifted your chin. Instinctively your eyes began to flutter shut, thinking he was going to bend his head and press those perfect lips against yours, but when words started leaving his mouth, you opened them.

“It’s a shame you’re a terrible hunter - your friend, too. I knew the moment you stepped into this little club that you were looking for me. However... I’ve grown to like you. You’re sweet, innocent. I bet your real kinky, too, but you hide it. So, darling... if you’d like, I’ve got a deal for you,” he murmured against your lips. When you stayed quiet, he continued. “You get rid of your annoying friend that’s waiting outside for me, and I’ll take you anywhere you want. I’ll please you, fuck you, all night if that’s something that interests you.”

All the air in your lungs left and the demon pulled away a bit. Your heart pounded in your ears, louder than the music playing, as you gasped and fought for air. You weren’t as stealthy as you thought you were and he knew it all along. Pink colored your cheeks as you tried to wrap your head around this new information.

“Think about all the possibilities, sweetheart. Me and you, my fingers in your sweet pussy, my cock in between those luscious lips as I fuck your mouth relentlessly... or how about I bury my cock in between those thighs of yours and watch your tits bounce? You could have all that and more if you get rid of that friend of yours.”

That filthy mouth of his was what sold you in the end. You nodded your head weakly as he told you a meeting point, five minutes away. Stumbling your way to the bar, you paid the bill and tipped the bartender before you left. Daisy was right where she said she’d be - waiting in the alley.

Her expression turned furious when she saw that you came back empty-handed.

“What the hell?” she exclaimed, throwing her hands into the air. “You were supposed to seduce him and _bring him back here_!”

You shrugged. “He wasn’t inside. I stayed to look for him, make sure I didn’t miss him. Guess he moved on, I don’t know.”

Daisy groaned, throwing her head into her hands. “Whatever, let’s just go.”

“Actually...” your voice stopped her completely. She slowly turned to face you, eyebrow quirked. “I might have met someone inside and... well... that’s also what took so long and I... might be...”

“Spit it out, Y/N,” she encouraged.

“I was planning on meeting up with them,” you whispered, teeth latching onto your bottom lip.

Daisy rolled her eyes before digging into her pockets. She pulled out a couple of silver packages before tossing them at you. You flipped them over in your hands, eyes widening and cheeks turning bright red when you realized what you were holding.

“If you’re gonna sleep with someone then be safe about it. When you get back, I want all the dirty details, you little minx,” Daisy instructed, smirking as she left you flustered.

_You’re not gonna like every detail, Daisy_ ,  you thought grimly before turning around and heading to the meeting point.


	10. Maid - Dean Winchester

**Summary for the Chapter:**

> A Halloween party leads to you and an old friend from high school catching up... in your own way.

**Notes for the Chapter:**

> Another one from a follower celebration from Tumblr. My favorite, of course. Also... Daisy happens to be one of my favorite names, so if you're wondering why I used to twice, there you go.

“This is so stupid,” you muttered, yanking at the material. “I  _ feel  _ stupid. Why did you make me do this again, Daisy?”

You turned to glare at your close friend who was dressed up somewhat similarly. Whereas she was wearing dressed up as Little Red Riding Hood, complete with a red corset, matching mini skirt, fishnet stockings and a red cape, yours was the stereotypical maid costume. You had the little black dress with a white apron, white choker, and stockings.

“Because you need to get over that jerk off of an ex-boyfriend, and getting laid by a super-hottie will help you do just that,” she said, rolling her eyes.

You picked at the outfit, looking down at it with disdain. “Looking like this is going to help? Why can’t I just be charming with a less… revealing outfit?”

“It’s Halloween, you’re allowed to wear revealing shit, okay? Quit whining and let’s get inside already,” she grumbled, latching her fingers onto your wrist and pulling you into the house you’d been invited to.

It was just as you expected the party to be – crowded, music pumping loudly, and alcohol in  nearly everyone’s hands. Sighing internally, you immediately started mingling like you knew your best friend wanted. If you played it her way for a while, you could  make some sort of excuse and escape. Just needed time and patience.

* * *

 

After an hour and a couple of beers, you were damn near ready to leave. The guys that were invited were getting on your nerves and you’d gotten pretty close to punching one for being disgusting and perverted. You only managed to escape when a buddy of his claimed his attention. Hopefully leaving for the other side of the crowd was enough to never run into him again.

Sighing, you sipped on the beer in your hand while your eyes scanned the crowd. Until they stopped on one individual.

_ Holy shit, that’s not him. _

Narrowing your eyes, you immediately recognized him. Those eyes, that dirty blond hair of his, and that damn leather jacket… it was also the lack of costume that made him stood out. Holy fuck did he age well. The last time you saw him was… well, when you were sixteen and you both were silly teenagers.

Immediately, you ducked your head and searched for your best friend. Finding her with a Snow White, you tugged on her arm to get her attention.

Leaning in to speak quietly despite the loud noise, you said, “Remember Dean from high school? The one I had the biggest crush on?”

Daisy’s eyebrows pulled together, confused. “Yeah? What ‘bout him?”

“He’s here.”

Daisy’s eyes nearly bugged out of her head as she immediately scanned the crowd for him. Her mouth drops open as she mouths, “Oh, my god,” silently. She turns to you with a devious grin.

“He is hot! Go over there and talk to him,” Daisy giggles, pushing you in his direction.

“No! Come with me,” you plead. After a second glance in his direction, you added, “Look, he isn’t alone either. The tall one that’s with him. Please?”

Daisy’s eyes scan the taller man next to him. Shaggy brown hair, definite muscle beneath the clothing, and an expression on his face that told her he did not want to be at this party anymore than Y/N did. She pursed her lips before turning back to you.

“Fine, only because he’s cute as hell,” she said as she latched onto your wrist again, pulling you in their direction.

* * *

 

You felt your heart hammering away in your chest as you neared Dean. Now that you were closer, you saw the corners of his lips curling into a smirk as his eyes scanned the crowd. The stubble on his jaw made you catch your breath. God if you thought he was fine as hell at sixteen, he was breath-taking now, especially with the stubble and that aged-look.

Dean Winchester was something else. How one man was blessed with such attractive looks, you weren’t sure.

When you finally reached him and his gaze settled on you, a blush spread across your cheeks. Smiling shyly at him, you grinned. “Hey, you’re Dean right? It’s Y/N, from high school.”

Recognition lit up his eyes.

“Right I remember you,” he said, his eyes scanning your body quickly. “What’re you doing here? Didn’t think you were one for partying much.”

You shrugged. “Daisy wanted to come out and I decided to accompany her.”

His eyes flickered to the woman next to you for a second then back to you. “Daisy, Y/N this is my little brother Sam,” he said, motioning back to the tall man next to him.

Your eyes flicker back to the man next to him and immediately memories of seeing Dean and a smaller kid following him around. Sam had definitely grown up. Teeth latched onto your bottom lip to keep yourself from saying anything embarrassing.

Daisy grinned, brought up a conversation with Sam and immediately, the two started walking away together.

“So, it’s been a while,” Dean smirked, bringing a bottle of beer to his lips. “Surprised you recognized me in a crowd like this.”

You shrugged. “Hard not to miss a person not dressed up.”

A subtle pink blush bloomed across his cheeks as he chuckled, glancing down as he rubbed his neck. “Yeah, I guess you’re right. Didn’t feel like dressing up, thought I could get away with wearing this. You’re dressed up, though.”

“Courtesy of Daisy,” you said, biting your lip.

You felt his eyes on you, scanning from the heels you wore, to the stockings and the flesh of your thighs, to the little skirt and apron, up to the cleavage that your costume allowed you to show, and up to the white choker around your neck.

“I should probably thank her then. You look gorgeous,” he grinned.

Ducking your head, you blushed and sipped from the drink in your hands. He glanced around the room, the corners of his mouth lifting slightly, before turned back to you.

“Wanna get out of here? It’s getting crowded.”

With a nod of your head, the two of you escaped the crowded house.

* * *

 

The two of you ended up on the roof of your apartment building, on the old couch you found up there. After heading into your apartment and snagging a blanket (because honestly, you didn’t trust how many people have sat on that couch before), you headed up there with him.

“So no one special?” he asked.

You shook your head. “Nah. Everyone I date ends up being a total jackass. Eventually I just quit dating completely. I take it you’re single too?”

Dean nodded his head. “Mhmm. The life I lead… it’s not the kind that allows me to settle down.”

You didn’t think he’d elaborate on that so you let it be, shrugging your shoulders. “Not a lot of people are able to settle down. It happens.”

For a while, neither of you spoke. Sipping on the drinks in your hands, you let your eyes flicker over the city skyline. It was one of the plus-sides of renting in this particular apartment building - it had a beautiful view of the city. After a while, Dean made a noise.

I turned to him with a questioning glance.

“I kind of miss high school,” he murmured, pursing his lips. “The simplicity of it all, you know? You’re just a kid with not much expectations. Nobody expects you to do much except do well in school and just enjoy bein’ a kid.”

“We can do that again, you know,” you raised an eyebrow as you spoke. Dean’s head swiveled to face you, a curious expression on his face. “Enjoy being young without any expectations. For tonight - if you want.”

The implications were there, the intention of what you wanted was all there. It was obvious the way you said it with your bottom lip latched between your teeth. All he had to do was say yes. Say yes and you could get your hands on him once more…

Slowly he moved towards you, eyes never leaving yours. He crawled on top of you, his solid, muscular body laid over yours. Dean tangled his fingers into your hair, leaning down so his lips were centimeters away from yours.

“Darling, this isn’t high school anymore,” he murmured. “I’ve learned a few more tricks than the last time we were together.”

Your head was immediately filled of the only time you had sex with Dean. The two of you were sixteen years old and definitely inexperienced. Even so, you loved every second of the sweating, mess of limbs the two of you’d become that night.

The thoughts in your head were cut off by a pair of soft lips meeting yours. Eagerly you kissed back, one hand sliding up his back to tangle in his locks of dirty blond hair. A moan escaped when the kiss deepened and intensified, tongues sweeping and tasting.

Dean pulled away, panting, and immediately started kissing down your jaw, sucking and biting as he went. He left marks along your skin, hands traveling across your body while never quite settling in one place. Slowly he began to slide down, lips kissing and sucking as he went.  Eyes rolling back, you moaned.

Fuck, he’s definitely improved, you thought.

He settled himself in between your legs, lips curling into a smirk as he stared up at you. Dean’s hands wrapped around your thighs, fingers just above the lining of the white stockings you’d worn, and squeezed your flesh.

Your breathing hitched, mouth falling open as he leaned down and kissed the crease between your legs and your cunt. Suddenly his lips were on your core and you were crying out, hands flying to his hair. You felt him chuckle, his stubble scratching at your skin.

Dean continued licking, sucking at your cunt. It was true what he said - he did learn a few new tricks since high school and goddamn did it work on you. It wasn’t long before you were arching your back, crying out Dean’s name as you came into his mouth.

As you panted, Dean crawled his way back up to you, kissing you softly on the mouth. You felt him bare against your heat, just pressing against you while Dean kissed you while you came down from your high.

“You good, baby?” he asked gently, running his fingers through your hair. When you finally nodded, he began sliding his cock up and down your soaked folds leaving you moaning and clutching at his shoulders.

“Fuck, did I ever tell you how  _ hot  _ you look dressed as a maid?” he murmured in your neck as he began to push himself inside your wet heat.

You whimpered, loving the filthy words that fell from those lips. His hips slammed into yours in a furious pace, too impatient to go slow with you. You didn’t mind, either. Still sensitive from your first orgasm, it wasn’t long before you felt the heat in your lower belly, the knot forming quickly.

“Dean,” you whimpered quietly as you heard him grunt into your neck. “I-I’m not gonna last.. I’m gonna.. gonna…”

And then you were coming for the second time that night, crying out as you arched into his body while feeling every muscle against you. Feeling you clench around his cock so tightly sent Dean into his own orgasm, moaning your name as you both relaxed into each other.

* * *

 

Falling asleep was easy. Dean was warm and he let you wrap yourself around him after getting dressed. He slid the blanket over the two of you, let his arm rest over your waist as you fell asleep.

The busy sounds of the city and the warmth of the sun had woken up you. A grin slipped onto your face as you stretched your body, expecting Dean to be nestled right up against you, in the same spot you’d fallen asleep in last night. But when you stretched yourself across the couch, you felt nothing.

Eyes flying open, you scanned the rooftop but he was nowhere in sight. Your heart sunk, the disappointment flooding you.

Dean  _ did  _ say the life he led left him little room to settle down. Plus you said it was for the night. It was clear to the both of you it was a one-night stand only, nothing permanent. But still, you couldn’t feel but disappointed that you were the only one who still felt something last night.

Sighing, you began to pick  up your mess and head down to your apartment. You completely missed the hand-written note Dean left for you, not noticing the piece of paper fall from the mess of blankets as you headed towards the door.

_ I’m sorry I couldn’t stay. My number, though, if you ever need me: xxx-xxx-xxxx _


	11. 5-Star Motel - Castiel

**Summary for the Chapter:**

> Instead of the grimy motels, you check into a five-star hotel with your boyfriend Cas.

**Notes for the Chapter:**

> The last celebration drabble from Tumblr. I know it's short and I honestly don't feel like continuing it... but I liked it a lot, so.

As you glanced around the room, you whistled appreciatively. The duffle bags in your hands dropped to the floor as you set your hands on your hips. Well this  _ definitely  _ wasn’t a dingy motel on the side of a freeway in a small-town. Oh, no - it was much,  _ much  _ better than that. A five star hotel had things your usual motel rooms didn’t have. Like decent water pressure in the shower.

As the thought crossed your mind, you were immediately stripping yourself of your clothes. Castiel, who was the only one with you, glanced in your direction and didn’t say a thing as he watched you strip down to your bare skin, a trail of clothes leading to the bathroom. The water turned on moments later, a dragged out groan following just seconds after.

He let you shower, knowing that it was one of the few things you were looking forward to most. A decent shower that would help out the knots in your back from the last night. He didn’t want to bother you.

A few minutes later though, he heard you shout, “Cas! Get in here!”

Within seconds he was inside the bathroom, eyes glancing around the room for any sign of danger. When he found none, his gaze landed on you. The shower was a big, stand-in with a slightly see-through glass. It blurred the details but he still saw your shape. A pink blush formed on his cheeks.

“Babe ditch your clothes and get in here. You’re a mess, too,” you called from the shower.

Castiel still could hardly believe he was with an amazing human like you. Since being human, you were the one that was there. The one who knew his backstory and still accepted him as he was. It wasn’t difficult to fall in love with you. The feelings were knew to him and you helped him get used to things.

Eight months and he felt pretty human by now... though he still awkward and getting used to certain things. Like sex. Sometimes he couldn’t get enough of holding you, touching you. He couldn’t imagine anything else in this human world feeling better than that.

Castiel opened the door and you turned your head to smile at him. Turning around you finished washing out the shampoo in your hair. When he was finally rid of his clothes, he stepped into the shower and closed the door behind him. He wrapped his arms around you, burying his face into the crook of your neck. You giggled and tried pulling away only to have him tighten his grip on you.

“Cas,” you protested, giggling more. “C’mon, this is the first time we’re in a nice hotel. And we’re dirty. You know we gotta clean up first.”

“Please,” he whispered in your ear. “I just want to touch you.”

Breathing unevenly, you had to take a moment to gather yourself after that. You turned around and felt his hardening length brush against your thigh. Resting your hands on his chest, you lifted your head.

“How ‘bout this? We finish this shower and get cleaned up, then you can touch me all you want.”

You saw his eyes darken as he nodded his head. He reached for a wash cloth and the small, hotel bottle of body wash. Castiel lathered it up and reached for you. Your breath hitched as he began scrubbing the dirt and grime from your skin. Your knees weakened as he ran the cloth over your breasts, having to lean against his chest to stay upright.

It was when his hands traveled lower, in between your thighs, that you moaned out loud. “Oh, Cas... you’re teasing me.”

As he bent down for better access, he kissed your hips and murmured against the skin, “You said we needed to wash up. I’m doing just as you said.”

Groaning, he washed your legs and made his way back up. Castiel turned you around and squeezed your ass as he trailed the washcloth upwards, going along your spine and then your shoulders. He kissed the spot below your earlobe and a shiver rippled through you.

“Rinse off,” he murmured, pulling himself away completely.

He watched you with hooded eyes as your hands traveled along your body, rinsing off the suds. Biting your lip, you let your fingers brush against your hardened nipples and then your curls, just brushing your clit once before a hand ripped your fingers away.

“No,” he said, his voice low and husky. You nodded your head obediently and lathered a second cloth with body wash.

As much as you want your hands to travel to certain regions, you kept yourself obedient and washed him along his chest and arms, shoulders and back... When it came to his backside, you couldn’t help but playfully swat it. He narrowed his eyes at you before you moved onto his legs.

Once finished, you tossed the washcloth aside and grinned at him. “I’ll be in the bedroom while you wash your hair and rinse off.”

Before he could argue, you were already out of the bathroom with a towel wrapped around you. After making sure there was a ‘do not disturb’ sign on the door, you began drying yourself off. You half-expected Castiel to be out by now after what you said... but since he was still taking his time, you decided to lay on the bed.

You dipped your fingers into your heat and felt how soaked you were. Biting back a moan, you let your hands wander across your body. You pinched your nipples and squeezed them just how Castiel did, let one hand travel to your thighs were you teased yourself. Only then did you allow yourself to sink your fingers into your folds. You moaned, quite loudly, at the feeling of your fingers inside you. You wanted bigger, though, so you stretched yourself and imagined it to be Castiel.

You swore as your fingers brushed against your g-spot, hips bucking automatically. Everything felt so good, you were lost in your own pleasure that you didn’t notice the water shut off or Castiel walk back into the room.

His voice reached your ears. “And what are you doing, starting without me?”

Your gaze met his and you swore again, your fingers stilling inside you.

 


	12. Little Black Dress & Grind (part two) - Crowley

**Summary for the Chapter:**

> Crowley's deal is everything you hoped for and more. (part two to Little Black Dress & Grind.)

After a couple minutes of walking down the street, the heat in your cheeks disappeared. Tucking your clutch tighter against your body, you crossed your arms against your chest and hurried down the street. The meeting place Crowley mentioned was just a couple blocks down from the club. You entered it into your phone and it happened to be a pizza place. Public. 

A few people jostled into you but you easily bypassed them and hurried on your way. By the time you arrived, you were in desperate need of food and it looked like Crowley was nowhere to be found. You headed inside, a little bell dinging above you. There was very little people around. Just a couple customers were sitting at small tables while a few workers busied themselves behind a long bar. 

As you stepped up, one of the workers greeted you with a smile. You ordered two slices of plain cheese pizza and a moment later, the worker slid the slices on a plate for you. Fishing around in your clutch for a five dollar bill and some spare change, you dug around for a moment before sliding the cash over. 

“Thank you,” you murmured just before heading towards one of the small tables. 

Sitting down, you immediately took a large bite of the pizza. It burned the roof of your mouth but the greasiness and cheesiness tasted so damn good that you didn’t care. Burning your mouth was one of your last worries. Within just a couple minutes you shoveled nearly half the pizza into your mouth.

A cough had brought your attention from the pizza in your hands. Glancing up with a mouthful of food, your eyes landed on the demon from before, Crowley. You swallowed the food in your mouth as he took the seat across from you.

Bashfully, you smiled at him. “Hi. I got a bit hungry. Sorry.”

Crowley shook his head. “No, darling. Don’t apologize. I’d actually rather you get some food into your system considering the amount of alcohol you consumed tonight.”

Cheeks heating up, you remembered that you had at least four drinks. Without saying anything though, you bit down onto the pizza again. The demon didn’t say much, just waited for you to eat your two slices and when you were nearly finished with the second, retrieved you a third slice. 

“I- you didn’t have to, Crowley,” you stammered.

“Hush, darling. Eat up,” he insisted, pushing the plate towards you.

You listened to him, partially because you were still intimidated by him. He was a demon and yet, he was sitting in front of you making sure you had food in your system. About halfway through your third slice of pizza, Crowley managed to get a couple bottles of water. 

When he came back, you raised an eyebrow.

He rolled his eyes. “I’m sobering you up. Now finish the pizza and drink these.”

After finishing the pizza you washed it down with one of the bottles of water. You already felt better and a lot more sober after getting a decent amount of food in you. It was only after downing half of the second bottle that Crowley was satisfied and believed you to be sober enough.

“C’mon,” he said, rising from the chair. His hand was held out to you. “There’s an apartment I have across the street.”

Allowing your hand to slip into his, he led you outside of the pizza place after throwing out your trash. The apartment he said he had was across the street just as he said. What he left out was that it was on the pricier side. You knew this the moment you stepped into the building.

No one except those with an exceptional amount of money would have been able to afford an apartment in the building. Crowley led you towards an elevator, hand pressed to the small of your back the entire time. Even when the elevators shielded you and put you both in your own little bubble, he didn’t remove his hand. Leaning forward a little, he pressed one of the buttons. 

The hum of the elevator started up just as it began to rise. Biting your bottom lip, you waited for the elevator doors to open. The longer you spent inside the elevator, the more you became nervous.

How often did you go for one night stands? Never. Most of the sex you had was either by your own hands or with your previous boyfriends. You weren’t used to having sex with someone with little to no emotional connection. Sure - the lust was there all right. You wanted nothing more than to feel Crowley on top of you as he fucked you senseless. But how could you get up hours after you had sex with someone and leave their lives as if the night never mattered? Was it possible?

The ding of the elevator opening cut off your thoughts. Crowley led you down a hallway, passing three separate doors until he stopped at the fourth one down. It was a plain door, nothing really special about it. But you had a feeling that beyond the door was decorated spectacularly. 

You weren’t disappointed.

His apartment looked like it came straight out of a magazine. But the way he had his apartment decorated wasn’t what blew you away. It was the amazing view he had of the city. Immediately, you stepped out of his touch and went to stand in front of the large window. 

Your fingers carefully trailed along the glass, your eyes glued to the view. It was a beautiful sight. Lights everywhere you looked, the cars zooming by below. You saw buildings alight far off into the horizon. Mouth agape, you just  _ stared _ , completely forgetting the other person in the room. 

Well, until you felt his arms snake around your middle and his lips trail along your shoulder. Lips parting, you felt his stubble graze your skin, causing goosebumps to appear. You shuddered as his lips travel towards your neck, sucking marks along the way. A moan slipped when he nipped at your earlobe, your own hands resting above his. 

“What’s got you nervous, darling?” he murmured against your skin.

“I’ve... I’ve never... had a one night stand before,” you said breathily.

He nipped at your skin again, squeezing your middle softly. “What’s there to be nervous about? Tonight I’ll make sure you never forget me or what happened between us. You’ll stammer on your words when you tell your friend all about me and what we've done. You'll get so turned on when you think about me...”

The words slipped from your mouth without hesitation. “You're pretty sure of yourself.”

“It’s a promise, darling,” he whispered into your ear.

With that said, Crowley turned you around and let his lips glide over yours. At first it was slow, languid almost. You kissed back, cupping the back of his neck to pull him closer. His hand slid down to your hips, squeezing them as the kisses heated up. It wasn’t long before tongues collided as your hands trailed along his clothes, taking them off piece by piece. 

You had to pull away from him, panting, in order to unbutton his dress shirt. When each button was undone, you slid your hands up his chest, over his shoulders and let the shirt fall to the floor. Crowley’s hands went south until he was gripping your thighs, just below the hem of the dress. And then he slowly started to pull the dress upwards, over your body and head. It landed behind him.

Crowley groaned as he cupped your breasts through your bra, running his thumb over the lace. “You had  _ this  _ underneath that dress the whole time?”

Shyly, you nodded your head. 

Daisy wanted you to go all out. That meant a matching, black see-through lingerie set. Cheeks heated up under his appreciative gaze. Crowley groaned before leaning down and gripping your thighs. He hoisted you up, your hands flying to his shoulders. Then he carried you throughout the apartment, kissing you heavily. You'd been so focused on kissing him and feeling his stubble underneath your hands that you had no idea you reached the bedroom until you fell down onto silk sheets. You gasped, looking up to see Crowley staring down at you with a heated, lustful gaze.

“Oh, sweetheart,” he moaned out, spreading your legs. “You look delicious.”

Then, before you could whip up a reply, Crowley bent his head and nipped at your thigh. You gasped, feeling his stubble brush against your skin. Almost immediately your hands gripped the sheets as he worked his way up to your clothed core. Crowley dug his fingers into the waistline of your panties and pulled down, tossing them over his shoulder. 

A moment later you felt his mouth on your core. You arched your back, gasping as you felt his tongue trace your folds. You felt him everywhere but the one place you needed him. Biting down on your bottom lip, you squirmed under his touch as you wanted more - no,  _ needed  _ more.

“Crowley,” you gasped, your grip on the sheets tightening, “Please, more!”

His nose nudged your clit, gripping your thighs tighter as his scruff brushed against your skin. You moaned, arched your back slightly, as pleas fell from your lips. He didn't let up though. Crowley teased you over and over again, never quite touching you in the places you wanted.

"Please fuck me with your fingers," you whimpered. 

His mouth detached from your wet core. "Why should I, sweetheart?"

Lifting your head a little, you stared at him as you cocked your head to the side. "Haven't I been a good girl?"

A low groan escaped his lips, and then suddenly, Crowley bent his head again. His fingers sunk into you easily, curling his fingers just right as he pumped you. Your head fell as a lewd moan echoed around the room. Just as you felt the familiar heat building, Crowley's lips suddenly reattached themselves to your core, sucking on your clit. Crying loudly, you arched your back high as you came hard around his fingers. 

After pushing you through the rest of your orgasm, he hovered over you and pressed his fingers against your lips. Obediently you opened your mouth and sucked on his fingers until they were clean of your arousal. 

"You've definitely been a good girl," Crowley whispered in the crook of your neck. "And good girls get rewarded, don't they?"

Before you could say anything, Crowley was beside the bed and tossing his own clothes around the room. After a moment he was in between your legs again, only this time he had one leg propped over his shoulder and then other hooked around his hip. You felt his hardened length pressing against your core.

Just as he started to enter, Daisy's words came back to you.

_ "If you're gonna sleep with someone then be safe about it." _

"Wait," you panted, glancing up at him shyly. "What about protection?"

Crowley pulled away a little, letting your legs fall. "If that's something you wish to have, then sure."

Biting your lip, you admitted, "I... I have a few in my clutch. Daisy... I had to tell my friend that I was going home with someone in order for her to leave me alone. She tossed 'em at me, really."

Crowley lifted you up, smirking just slightly, and told you, "Go get them, sweetheart."

You walked half-naked throughout his apartment. As you went, you gathered up the few pieces of your clothing you found. Like your dress by the window. Your panties were still in the bedroom, though. As you reached the couch, where you found your clutch, you folded up your dress and undid clasped your bra. You tossed it on top of the dress before you searched through your clutch for the silver packages.

When you appeared back in the bedroom, you were met with quite a sight. Crowley leaned against the headboard, lazily stroking his large cock. Licking your lips, you tossed the packages onto the bed and crawled in between his legs. You swatted his hands away and replaced them with your mouth. 

Almost immediately, Crowley tangled his fingers into your hair and guided you along his cock. You kept your jaw relaxed as he pushed you down further until you were gagging. His grip on your hair relaxed and you slowly rose up to let yourself breath a little. It continued like this a few times – Crowley guiding your mouth along his cock, pushing down until you were gagging, and letting you up to breathe. 

Eventually though you reached for a silver package and ripped it with your teeth. Slowly you slid the condom over his length and wrapped your lips around him again. This time, though, he only let you suck him off for a minute before he was pulling away.

"As much as I'm enjoying this," he murmured as he pushed you onto your back, "I've gotta have you, sweetheart."

One leg was propped against his shoulder and the other wrapped around his hip like before. With one quick thrust, he was inside you and stretching you in ways you haven't been before. You gasped and clutched onto the soft sheets, fists tightening as Crowley began fucking you. His pace picked up considerably when you finally relaxed around him and then, your cries were echoing around the room. 

Even with the laced, see-through black bra your breasts bounced each time Crowley thrusted his hips into you. You cursed as you held onto the sheets, your hands eventually moving to the headboard. Teeth latching onto your bottom lip, you whined lowly.

“What is it my pet?” Crowley growled as his hands tightened on your hips, almost enough to leave bruises. “What’s got you whining, hm?”

“I’m-” you cried out as soon as you felt him hit a particular spot. “Oh,  _ fuck _ , Crowley! I’m gonna come, I’m gonna...”

You were trembling as you felt your climax approaching. The stretching of a rubber band, being pulled until there was no way it could be stretched any further. Then a snap, and you were crying out, arching your back into Crowley’s chest, as you came.

Faintly you were aware, in your post-orgasmic bliss, of Crowley groaning your name as he came. With the slight pain you felt on your hips, you knew you’d be bruising well for at least a few days maybe a week. Daisy would no doubt notice them and the sting each time you’d sit down. She’d tease you, no doubt.

Eyes slipping shut, you were aware that Crowley had pulled out already and was beginning to wipe you down with a warm, wet cloth. You hummed quietly, curling up when he pulled away.

"It's all right, sweetheart," you felt his hand cup your cheek as your eyes drifted close. "You can go to sleep."

Your limbs felt heavy and you were too exhausted to gather the strength to walk across his apartment and get dressed. So you let your eyes shut and sleep take you. When you woke up though, you had to blink a few times to adjust to your surroundings. The state of the bedroom and the lack of clothing you wore was enough to remember last night's events.

Quietly you snatched your underwear from the floor and slipped them on. Before you opened the door, you wrapped a sheet around your half-naked form and immediately headed for the couch. Heart pounding, you searched for any sign of Crowley. But the demon was nowhere to be seen. You sighed quietly, shoulders sagging in relief.

You weren't used to sneaking out of someone's place in the morning. Running into Crowley was the last thing you wanted. 

Regardless though you slipped on your bra and dress as fast as you could, slid your feet into your heels and grabbed your clutch. You made your way to the door as you attempted to fix the tangled mess of hair atop your head. As you opened the door though, you glanced around the room one last time.

This was definitely one night you'd never be able to forget.


	13. Little Tease - Sam Winchester

**Summary for the Chapter:**

> Sam has missed Y/N while she was overseas for over a month helping an old friend with a hunt. After a month of teasing and some very pornographic texts, she arrives at the bunker is welcomed home

**Notes for the Chapter:**

> Okay I didn’t realize it was partially written in second and third person until I was halfway into the fic. I’d edit it and change it but to be honest, I am way too lazy to do so. Plus I like the way it is. Hope you guys liked this!

The first real sex-scene in this chapter is inspired by [this gif-set](https://sinister38.tumblr.com/post/162805102868/adios-tumblr). Beware, it's super super pornographic and on Tumblr, so.

* * *

 

When Y/N left for Europe her relationship with Sam was simply friendship. At least, that’s how she saw it as. A friendship with a man she’s had one-sided feelings for far too long. Maybe she hoped that on her long trip overseas would help change her feelings for the younger Winchester, but in fact... they didn’t. It did the opposite, especially when the night Sam butt-dialled her.

His contact showed up on her phone and without hesitation, she slid her thumb over the green button and pressed accept. As she held her phone to her ear, guttural groans filtered into her ear. Y/N blinked twice before she pulled the phone away from her and stared it. Hesitantly she put the phone back and heard a soft moan.

“Sam?” she quietly asked.

He didn’t reply to her. In fact, it was as if he didn’t hear her at all. There was panting, heavy with the occasional grunt, before she heard a few quite audible profanities. Heat spread across Y/N’s cheeks as realization dawned on her. Sam must have accidentally butt-dialed her while jacking off.

Just as she was about to pull away, she heard Sam moan out, “Fuck... Y/N, right there... Right there, baby. Oh god.”

A wave of arousal hit her as she heard her name falling from his lips. Squeezing her thighs together, she hung up the phone and bit down on her lip. She considered whether or not to send a message. But the sound of Sam moaning her name... she couldn’t forget it even if she wanted to.

_ Y/N  _ – _ you butt-dialled me on accident. Next time you wanna get off, you can always ask me for pictures or help instead of imagining things. I wouldn’t say no to that. :* _

_ Y/N  _ – _ PS, hearing you moan my name was hot. _

She wondered if she took it too far by sending those messages but instead of overthinking and worrying about it, she turned her attention back to the books she was trying to interpret. It was another half-hour of work before her phone dinged. Hesitantly she picked it up and unlocked it.

_ Sam  _ – _ I’m gonna take you up on that offer. _

The corners of her mouth curled into a grin.

\-----

It was only a week later that Sam texted her, asking if that offer was real. It had Y/N grinning from ear to ear as she made a vague excuse to her friend. By the time Y/N reached her motel she was antsy with anticipation. Locking the door behind her, she threw her bag on the floor before she opened her phone.

_ Y/N – Sure thing... as long as I get something in return. _

_ Sam – I think that can be arranged. _

As quickly as possible, Y/N began stripping herself of her clothes. Once she was only in her panties she grabbed her phone and pressed record. Y/N managed to keep the camera below her shoulders as she filmed herself cupping her breasts and teasing her nipples with her forefinger and thumb. She moaned softly, just loud enough for her phone to pick it up, as her hand slowly skirted her ribs and trailed down. Y/N angled her phone to show her legs and her pink panties.

As she dipped her fingers beneath the waistband, she whimpered as she slipped them into her soaked folds. For Sam's benefit, she said, "Fuck, Sammy. I'm so wet and just for you. Wish you could feel how soaked I am."

After that she ended the video and sent it to him. But she never retreated her fingers from her cunt, though. Slowly she played with herself hoping that he'd return the favor. Biting down on her lip, she waited patiently while slowly building to her own release.

At last though her phone dinged twice, one a text message and the second a video message. Skipping over the text message, she went straight to the video. Pressing play, she eagerly watched.

The first thing she saw was Sam's erect cock with his hand wrapped around it. Y/N's jaw dropped at the size of his cock. It was long and thick enough without hurting her too much. His tip was red, angry and leaking precum. His wrecked moans could be heard as he stroked himself. Y/N moaned helplessly as she moaned, circling her clit faster while keeping time with Sam's strokes.

The pressure was building quickly, her thighs tensing up as she felt her release coming quickly. But that's when Sam's filthy moans turned into groans and grunts. Y/N felt her heart racing as she was just on the edge when hot spurts of come dripped over Sam’s toned and well-muscled chest.

That was the breaking point. Y/N cried out softly as she came, arching her back as waves of pleasure washed over her. When she finally was able to focus properly she picked up her phone and read the text message.

_ Sam  _ –  _ That’s one hell of a video, baby. I fucking loved it.  _

Y/N grinned, pleased that he actually liked it. Quickly she snapped a picture of her lower half and sent it to him with the caption: “And I loved yours, as you can clearly see. Made such a mess.”

\---

From that point on, you made it goal to send Sam risky selfies during your trip. You sent him a sexy selfie a couple days later. There was just enough in the selfie to see a little bit of cleavage to remind Sam how her breasts looked in the video. A teaser. She sent him another one a few days after that, one of her in complete lingerie. Lacy bra and panties to garters and stockings. The picture included her in the only heels she had with her. It was lucky she had to pack for a charity ball knowing she had to attend one with her friend, otherwise she wouldn’t have been able to take that picture. 

That’s how Y/N spent the rest of the month - teasing the living shit out of Sam with selfies. And on the phone, when she knew Dean was nowhere around, whispered filthy fucking things into the phone. Things she wanted to do to Sam when she got back. Promises of long, sweat-filled nights. 

But Sam played just as dirty, too. One night while they were on the phone with each other, Y/N happened to let it slip that she had a thing for his arms. He’d laughed, a little confused, and asked her what it was about his arms. She had bit her lip while heat filled her cheeks. 

“I dunno,” she said shyly. “They’re just... well, yanno...”

“No, I don’t know,” Sam said. She could sense the smirk on his face and grew even more shy at the sound of his low, gravelly voice. “Tell me, Y/N. I wanna know.”

She stuttered, cursing Sam silently, “It’s... it’s a turn on, seeing your biceps. K-knowing you could easily pick me up and manhandle me.”

Sam groaned, muttering a profanity under his breath.

That night was spent listening to each other’s groans and whimpers as they both got off to the filthy words coming out of the other’s mouth. It was a spectacular night. One that promised better things to come when Y/N got back to the States.

By the time the month was up, Y/N was a frustrated and horny mess. Her fingers hardly satisfied her anymore, leaving her wanting for more each time. It was just unfortunate she left all her toys at home. On a hunting trip, she didn’t think she’d need time. 

As she drove closer and closer to the bunker, Y/N felt the excitement and anticipation growing. All she wanted was Sam on top of her, touching her everywhere. She sighed just thinking about it. By the time she arrived, she decided she would head to her bedroom and use her toys if Sam wasn’t around. There was no way the night wouldn’t end with her orgasmsing multiple times.

The garage was empty, Impala gone. Y/N sighed, running a hand over her face. Maybe the boys went on their own hunting trip while she was gone. Maybe it was for the best. She was too wound up to be around Sam if he wasn’t planning on fucking her into the mattress.

Dropping her duffle bags onto the table, she headed straight for the kitchen for some well needed food. She poured herself a glass of water, guzzling half the glass almost straight away. Just as she set it down, Y/N felt two large hands being placed on her hips.

Without turning around she knew exactly who was standing behind her. His lips ghosted over her ear before he nipped at her earlobe gently. Breathing shakily, she let her hands rest over his. 

Sam whispered, “Dean’s gone to a bar and I won’t expect him to be back tonight. What do you say?”

“Yes,” Y/N said as you slowly ground her ass into his crotch. She could already feel his hard length strained in his jeans. Remember seeing it on video had her aching for it. Wanting to feel it in her hands, the hot skin as she stroked it gently before wrapping her lips around the head of his cock and began tasting him. 

She couldn’t help but moan at the thought of having him in her mouth. Eventually they’d get there. Whether it be hours later or another day. She was planning on taking Sam’s wonderful cock into her mouth. 

His hands slipped out from underneath hers as he unbuttoned her jeans. Y/N’s breathing became heavier, clutching the counter as he let his fingers play with the waistline of her panties. At the same time, Y/N felt his breath hitting the crook of her neck. Biting down on her bottom lip she knew she was being teased and fuck was it working. So much anticipation happened over the month that led to this moment. And all she wanted was for him to take her against the counter. They had the rest of the night to explore each other’s bodies.

“Sam,” her voice barely a whisper. “Fuck me, please. I want you so bad, please just fuck me.”

“Not yet,” he replied, voice gruff. She started to protest but Sam hushed her. “Do you trust me, princess? I’ll take care of you and make you feel real good.”

Y/N nodded her head quickly. As long as she got some sort of release soon she didn’t care how it was done. Sam slowly pulled down her jeans until they pooled at her ankles, followed by her panties. He rested his hand on Y/N’s chest, his fingers just barely brushing the base of her neck as he held her against his chest. His other hand, however, delved into her wet folds. 

He groaned as he circled his fingers into her heat. “Fuck, princess, you are so soaked. Have you been waiting for this? Have you been a horny little girl?”

Y/N whimpered, growing even wetter at the dirty talk - a favorite of hers. “Fuck... yes. Been waiting all month for you to fuck me senseless.”

Sam sunk his fingers deeper into her, a low moan coming from Y/N as he slowly pumped his fingers inside of her. Just slightly her legs parted for better access. She groaned softly as he ground his crotch against her ass. 

“I’m gonna try something, okay?” he said as he pulled his hands away from her. She whimpered, about to protest, when the sound of the zipper shut her up. The sound of clothes hitting the floor reached her ears. 

Her breathing quickened as she felt Sam’s hard cock pressed against her ass. He kissed the skin just below her ear as he whispered, “D’you trust me?”

“Yes,” she answered.

With that, he slid in between her thighs. The head of his cock just barely brushed her clit by the time his hips met the flesh of her ass. He repeated it, over and over again, sliding his cock in between her folds and thighs while never truly penetrating her. It was teasing and satisfying at the same time. 

Y/N groaned and kept her thighs pressed together while she gripped on tighter to the counter. With each thrust it brought her closer to release. It wasn’t long before Sam’s cock was soaked in a mix of his own precome and Y/N’s arousal. It only made it more pleasurable, had both of them on the edge as they were just moments away from coming.

A low whine escaped Y/N’s throat, feeling herself about to come. “Sammy! Fuck, right there. Oh god, don’t stop, don’t stop!”

With that her thighs trembled as she fought to stay up right, coming all over his cock. Moments later, Sam’s grip on her waist tightened as he groaned into her skin. He came all over her thighs, his come dripping down. 

Once Sam managed to catch his breath, he kissed along Y/N’s throat and jawline. “Baby, go shower and relax for a little bit. I’m sort of hungry and I bet you are too. I’ll be in the bedroom in a bit with some food.”

After playfully swatting her ass, Y/N went and showered as Sam told her to. She was much more relaxed once Sam got his hands on her. Whatever he planned to do for the rest of the night she would happily oblige as long as it included a few more rounds of sex. She wasn’t quite ready to give him up yet.

 


End file.
